Herein, o-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The o-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglycosides exhibited high reactivity and glycosylation yields when N-iodosuccinimide and trifluoromethanesulfonic acid were used as promoters. Glycosylation with these thioglycosides in dichloromethane showed similar reactivity and stereoselectivity as those of phenyl thioglycosides. Glycosylation with per-O-benzyl salicyl-type thioglycosides in dichloromethane showed 1,2-cis-selectivity, while the same reaction in nitriles afforded predominantly 1,2-trans glycosides. In contrast, glycosylation with per-O-benzoyl thioglycosides afforded exclusively 1,2-trans glycosides. These results strongly suggest that salicyl-type thioglycosides can serve as non-malodorous alternatives for phenyl thioglycosides.
{"title":"Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis","authors":"Hirofumi Dohi , Risa Sakurai , Manami Tamura , Ryota Komai , Yoshihiro Nishida","doi":"10.1080/07328303.2021.1921787","DOIUrl":"10.1080/07328303.2021.1921787","url":null,"abstract":"<div><p>Herein, <em>o</em>-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The <em>o</em>-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglycosides exhibited high reactivity and glycosylation yields when <em>N</em>-iodosuccinimide and trifluoromethanesulfonic acid were used as promoters. Glycosylation with these thioglycosides in dichloromethane showed similar reactivity and stereoselectivity as those of phenyl thioglycosides. Glycosylation with <em>per</em>-<em>O</em>-benzyl salicyl-type thioglycosides in dichloromethane showed 1,2-<em>cis</em>-selectivity, while the same reaction in nitriles afforded predominantly 1,2-<em>trans</em> glycosides. In contrast, glycosylation with <em>per</em>-<em>O</em>-benzoyl thioglycosides afforded exclusively 1,2-<em>trans</em> glycosides. These results strongly suggest that salicyl-type thioglycosides can serve as non-malodorous alternatives for phenyl thioglycosides.</p></div><div><h3>Graphical Abstract</h3><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (190KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 1","pages":"Pages 45-65"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1921787","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49516487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.1080/07328303.2021.1975733
Jizhao Xie , Li Qiu , Luhui Zou , Yunfeng Xie , Di Luo , Huanji Xu , Xinduo Wu , Lisheng Wang
A novel protein-polysaccharide conjugate NFP-A4 was isolated and purified from water extracts of Nervilia fordii. The polysaccharide chain of NFP-A4 was found to contain D-galacturonic acid, D-galactose, D-glucose, L-arabinose, D-glucuronic acid, L-rhamnose, and D-mannose. The protein content of NFP-A4 was determined to be 12.83%, and it was bound to the polysaccharide chain via O-linkages at the serine and threonine residues. NFP-A4 was found to significantly activate macrophages and also induce immunomodulatory responses. These data suggest that NFP-A4 is a major bioactive component of N. fordii and may be responsible for many of its therapeutic properties.
{"title":"Purification, structural elucidation and immunostimulatory effect of a new protein-polysaccharide conjugate produced by Nervilia fordii","authors":"Jizhao Xie , Li Qiu , Luhui Zou , Yunfeng Xie , Di Luo , Huanji Xu , Xinduo Wu , Lisheng Wang","doi":"10.1080/07328303.2021.1975733","DOIUrl":"10.1080/07328303.2021.1975733","url":null,"abstract":"<div><p>A novel protein-polysaccharide conjugate NFP-A4 was isolated and purified from water extracts of <em>Nervilia fordii.</em> The polysaccharide chain of NFP-A4 was found to contain D-galacturonic acid, D-galactose, D-glucose, L-arabinose, D-glucuronic acid, L-rhamnose, and D-mannose. The protein content of NFP-A4 was determined to be 12.83%, and it was bound to the polysaccharide chain via <em>O</em>-linkages at the serine and threonine residues. NFP-A4 was found to significantly activate macrophages and also induce immunomodulatory responses. These data suggest that NFP-A4 is a major bioactive component of <em>N. fordii</em> and may be responsible for many of its therapeutic properties.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (370KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 5","pages":"Pages 226-242"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44097282","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-02-01Epub Date: 2019-11-29DOI: 10.1007/s13555-019-00344-z
De-Cong Zhu, Ye He, Zhe-Xiang Fan, Jin Wang, Qian Qu, Zhi-Qi Hu, Yong Miao
Introduction: Beard hair serves as an important additional donor supply to support hair transplantation in hirsute patients with extensive alopecia and lacking sufficient occipital hair. However, the efficacy and safety of large-scale beard hair extraction have not been studied extensively in the East Asian population.
Methods: Data obtained from hirsute patients with extensive alopecia who underwent hair transplantation between March 2017 and December 2018 at Nanfang Hospital were analyzed. Occipital and beard hair were evaluated separately during the pre-, intra-, and post-operative periods. Individual beard hair follicular units (FUs) were harvested under tumescence using a hollow punch with an outer diameter of 0.8-0.9 mm. Follow-up examinations were scheduled at 3-5 days, 1 month, and 9 months postoperatively to check for complications, determine the survival rate of mixed, transplanted FU grafts, and assess patient satisfaction. Data were collected and analyzed statistically.
Results: A total of 36 hirsute, male patients with advanced androgenetic alopecia (AGA) (Norwood-Hamilton V-VI) were included in this study. The density of the occipital and beard areas was 78.6 ± 4.6 and 48.4 ± 9.3 FU, respectively. It took 3.1 ± 0.9 h to harvest 3135 ± 863 FUs from the occipital area and 2.1 ± 0.6 h to harvest 2352 ± 599 FUs from the beard area. The transection rate for occipital FUs and beard FUs was 3.7 ± 0.4 and 3.9 ± 0.2%, respectively. Completion of the operation took approximately 10.0 ± 0.9 h, and no serious complications were reported 5 days after the procedure. An FU survival rate of 95.7 ± 1.6% was observed at 9 months after transplantation, with no visible hypopigmented scars observed in the bare areas. All patients were satisfied with the resulting cosmetic appearance.
Conclusion: Large-scale beard extraction, when combined with occipital hair extraction, is a safe and effective treatment to enhance the cosmetic appearance of East Asian men with advanced AGA.
导言:胡须毛发是多毛患者大面积脱发和枕部毛发不足时进行毛发移植的重要补充供体。然而,在东亚人群中,大规模提取胡须毛发的有效性和安全性尚未得到广泛研究:分析了2017年3月至2018年12月期间在南方医院接受毛发移植手术的多毛广泛脱发患者的数据。在术前、术中和术后分别对枕部毛发和胡须毛发进行评估。使用外径为 0.8-0.9 毫米的空心打孔器,在膨化条件下提取单个胡须毛囊单位(FU)。在术后 3-5 天、1 个月和 9 个月进行随访检查,以检查并发症,确定混合移植的 FU 移植物的存活率,并评估患者的满意度。收集数据并进行统计分析:本研究共纳入了 36 名多毛的男性晚期雄激素性脱发(AGA)患者(诺伍德-汉密尔顿 V-VI)。枕部和胡须部位的密度分别为 78.6 ± 4.6 FU 和 48.4 ± 9.3 FU。从枕部采集3135±863个FU需要3.1±0.9小时,从胡须部采集2352±599个FU需要2.1±0.6小时。枕部 FU 和胡须 FU 的横切率分别为 3.7 ± 0.4% 和 3.9 ± 0.2%。手术完成时间约为 10.0 ± 0.9 小时,术后 5 天未报告严重并发症。移植后 9 个月,FU 存活率为 95.7 ± 1.6%,裸露区域未发现明显的色素沉着疤痕。所有患者都对手术后的外观效果表示满意:结论:大面积胡须提取与枕部毛发提取相结合,是一种安全有效的治疗方法,可改善东亚男性晚期 AGA 患者的外观。
{"title":"Large-Scale Beard Extraction Enhances the Cosmetic Results of Scalp Hair Restoration in Advanced Androgenetic Alopecia in East Asian Men: A Retrospective Study.","authors":"De-Cong Zhu, Ye He, Zhe-Xiang Fan, Jin Wang, Qian Qu, Zhi-Qi Hu, Yong Miao","doi":"10.1007/s13555-019-00344-z","DOIUrl":"10.1007/s13555-019-00344-z","url":null,"abstract":"<p><strong>Introduction: </strong>Beard hair serves as an important additional donor supply to support hair transplantation in hirsute patients with extensive alopecia and lacking sufficient occipital hair. However, the efficacy and safety of large-scale beard hair extraction have not been studied extensively in the East Asian population.</p><p><strong>Methods: </strong>Data obtained from hirsute patients with extensive alopecia who underwent hair transplantation between March 2017 and December 2018 at Nanfang Hospital were analyzed. Occipital and beard hair were evaluated separately during the pre-, intra-, and post-operative periods. Individual beard hair follicular units (FUs) were harvested under tumescence using a hollow punch with an outer diameter of 0.8-0.9 mm. Follow-up examinations were scheduled at 3-5 days, 1 month, and 9 months postoperatively to check for complications, determine the survival rate of mixed, transplanted FU grafts, and assess patient satisfaction. Data were collected and analyzed statistically.</p><p><strong>Results: </strong>A total of 36 hirsute, male patients with advanced androgenetic alopecia (AGA) (Norwood-Hamilton V-VI) were included in this study. The density of the occipital and beard areas was 78.6 ± 4.6 and 48.4 ± 9.3 FU, respectively. It took 3.1 ± 0.9 h to harvest 3135 ± 863 FUs from the occipital area and 2.1 ± 0.6 h to harvest 2352 ± 599 FUs from the beard area. The transection rate for occipital FUs and beard FUs was 3.7 ± 0.4 and 3.9 ± 0.2%, respectively. Completion of the operation took approximately 10.0 ± 0.9 h, and no serious complications were reported 5 days after the procedure. An FU survival rate of 95.7 ± 1.6% was observed at 9 months after transplantation, with no visible hypopigmented scars observed in the bare areas. All patients were satisfied with the resulting cosmetic appearance.</p><p><strong>Conclusion: </strong>Large-scale beard extraction, when combined with occipital hair extraction, is a safe and effective treatment to enhance the cosmetic appearance of East Asian men with advanced AGA.</p>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"7 1","pages":"151-161"},"PeriodicalIF":3.4,"publicationDate":"2020-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6994566/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81728823","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2020.1837150
Lin Wang , Zhijie Fang
A series of deoxynojirimycin-triazole hybrid iminosugars had been prepared and investigated against a panel of glucosidases. Compound 10f (IC50 = 0.063 ± 0.006 mM) exhibited improved inhibitory potency against α-glucosidase compared to 1-deoxynojirimycin (IC50 = 0.155 ± 0.015 mM). Moreover, analysis of the kinetics of enzyme inhibition by using Lineweaver–Burk plots indicated that 10f inhibited α-glucosidase in a competitive manner. Compound 10m displayed moderate inhibition of α-glucosidase and β-glucosidase. The structure-activity relationships indicated that the introduction of the phenyl group and the nature of 4-position substituents on the phenyl ring had significant effects on the glucosidase inhibitory potency of the compounds.
{"title":"Exploring substituent diversity of deoxynojirimycin–triazole hybrid iminosugars: Discovery of potent glucosidase inhibitors","authors":"Lin Wang , Zhijie Fang","doi":"10.1080/07328303.2020.1837150","DOIUrl":"10.1080/07328303.2020.1837150","url":null,"abstract":"<div><p>A series of deoxynojirimycin-triazole hybrid iminosugars had been prepared and investigated against a panel of glucosidases. Compound <strong>10f</strong> (IC<sub>50</sub> = 0.063<!--> <!-->±<!--> <!-->0.006 mM) exhibited improved inhibitory potency against α-glucosidase compared to 1-deoxynojirimycin (IC<sub>50</sub> = 0.155<!--> <!-->±<!--> <!-->0.015 mM). Moreover, analysis of the kinetics of enzyme inhibition by using Lineweaver–Burk plots indicated that <strong>10f</strong> inhibited α-glucosidase in a competitive manner. Compound <strong>10m</strong> displayed moderate inhibition of α-glucosidase and β-glucosidase. The structure-activity relationships indicated that the introduction of the phenyl group and the nature of 4-position substituents on the phenyl ring had significant effects on the glucosidase inhibitory potency of the compounds.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 8","pages":"Pages 415-436"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1837150","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42871909","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2019.1708374
Rahul R. Nikam , Kiran R. Gore
Here, we report a highly selective, efficient and rapid method for the selective cleavage of primary acetonide using silica supported polyphosphoric acid (PPA-SiO2) for various carbohydrate substrates. Corresponding diols were obtained in good to excellent yields within 30 min using PPA-SiO2. Overall, PPA-SiO2 was found to be a useful catalyst for selective acetonide cleavage in carbohydrate substrates which may expand its utility in organic synthesis.
{"title":"A mild and convenient approach for selective acetonide cleavage involved in carbohydrate synthesis using PPA-SiO2","authors":"Rahul R. Nikam , Kiran R. Gore","doi":"10.1080/07328303.2019.1708374","DOIUrl":"10.1080/07328303.2019.1708374","url":null,"abstract":"<div><p>Here, we report a highly selective, efficient and rapid method for the selective cleavage of primary acetonide using silica supported polyphosphoric acid (PPA-SiO<sub>2</sub>) for various carbohydrate substrates. Corresponding diols were obtained in good to excellent yields within 30 min using PPA-SiO<sub>2</sub>. Overall, PPA-SiO<sub>2</sub> was found to be a useful catalyst for selective acetonide cleavage in carbohydrate substrates which may expand its utility in organic synthesis.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 2","pages":"Pages 63-74"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1708374","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45647990","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2019.1669633
Marijana Petković , Jenny Leopold , Iva Popović , Dušan Dimić , Jelica Ilić , Miloš Nenadović , Zlatko Rakočević , Jürgen Schiller
In this work, the performances of two ionic liquid matrices (ILMs) with the same ammonium counterpart for mass spectrometric analysis of the insoluble and soluble sucralfate were compared. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was performed assisted by the butylammonium salts of α-cyano-hydroxycinnamic acid (CHCAB) and 2,5-dihydroxybenzoic acid (DHBB). CHCAB has a higher IE than DHBB, but better optical properties. CHCAB is more suitable for the analysis of sucralfate, although molecular ions of both compounds were detectable only with low intensities. Thus, optical properties of ILMs are crucial to enhance the sensitivity of MALDI MS detection of polysulfated oligosaccharides.
{"title":"Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate","authors":"Marijana Petković , Jenny Leopold , Iva Popović , Dušan Dimić , Jelica Ilić , Miloš Nenadović , Zlatko Rakočević , Jürgen Schiller","doi":"10.1080/07328303.2019.1669633","DOIUrl":"10.1080/07328303.2019.1669633","url":null,"abstract":"<div><p>In this work, the performances of two ionic liquid matrices (ILMs) with the same ammonium counterpart for mass spectrometric analysis of the insoluble and soluble sucralfate were compared. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was performed assisted by the butylammonium salts of α-cyano-hydroxycinnamic acid (CHCAB) and 2,5-dihydroxybenzoic acid (DHBB). CHCAB has a higher IE than DHBB, but better optical properties. CHCAB is more suitable for the analysis of sucralfate, although molecular ions of both compounds were detectable only with low intensities. Thus, optical properties of ILMs are crucial to enhance the sensitivity of MALDI MS detection of polysulfated oligosaccharides.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 1-23"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1669633","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44092757","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2020.1839479
Chunjun Qin , Zhonghua Liu , Meiru Ding , Juntao Cai , Junjie Fu , Jing Hu , Peter H. Seeberger , Jian Yin
Pseudomonas aeruginosa O11 O-antigen is immunologically active but an exact protective epitope has not yet been identified. Synthesis of O11 O-antigen trisaccharide is of importance for identifying the epitopes. Here, neighboring electron-donating effects are keys to enhance the nucleophilicity of the C3 hydroxyl groups of D- and L-fucosamines, to facilitate the efficient synthesis of the trisaccharide. The disarmed peracetylated glycosyl donor with low glycosylation reactivity and glycosyl trifluoroacetimidate with good stability allowed for the glycosylation under mild conditions. The C6 nucleophilic tosylate substitution of D-galactose with iodine was found to be dependent on the steric effect of the axial C4.
铜绿假单胞菌O11 o抗原具有免疫活性,但确切的保护性表位尚未确定。O11 o -抗原三糖的合成对确定抗原表位具有重要意义。在这里,邻近的给电子效应是增强D-和L-聚焦胺的C3羟基亲核性的关键,从而促进三糖的高效合成。低糖基化反应活性的去武装过乙酰化糖基供体和稳定性好的三氟醋醋酯糖基可以在温和条件下进行糖基化。用碘取代d -半乳糖的C6亲核tosylate依赖于轴向C4的空间效应。
{"title":"Chemical synthesis of the Pseudomonas aeruginosa O11 O-antigen trisaccharide based on neighboring electron-donating effect","authors":"Chunjun Qin , Zhonghua Liu , Meiru Ding , Juntao Cai , Junjie Fu , Jing Hu , Peter H. Seeberger , Jian Yin","doi":"10.1080/07328303.2020.1839479","DOIUrl":"10.1080/07328303.2020.1839479","url":null,"abstract":"<div><p><em>Pseudomonas aeruginosa</em> O11 O-antigen is immunologically active but an exact protective epitope has not yet been identified. Synthesis of O11 O-antigen trisaccharide is of importance for identifying the epitopes. Here, neighboring electron-donating effects are keys to enhance the nucleophilicity of the C3 hydroxyl groups of D- and L-fucosamines, to facilitate the efficient synthesis of the trisaccharide. The disarmed peracetylated glycosyl donor with low glycosylation reactivity and glycosyl trifluoroacetimidate with good stability allowed for the glycosylation under mild conditions. The C6 nucleophilic tosylate substitution of D-galactose with iodine was found to be dependent on the steric effect of the axial C4.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 8","pages":"Pages 374-397"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1839479","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47356855","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2019.1663204
Jassem G. Mahdi , Hanaa M. Dawoud , Abigail J. Manning , Harvey F. Lieberman , David R. Kelly
Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at exo-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose 6 produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose 7. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound 7.
1,6-无羟基-β- d -葡萄糖吡喃糖衍生物的立体选择性光溴化发生在外显式h6。然而,4-苯甲酰-2,3-异丙基-1,6-无水-β- d -甘露吡喃糖6的光溴化反应产生了不稳定的4-苯甲酰-1,6-无水-3-酮-β- d -甘露吡喃糖7。C-3的立体选择性氧化机理可归因于C-3的易自由基质子萃取,随后异丙基的溴化,随后在水处理过程中被消除。因此,本文的目的是鉴定不稳定化合物7的分子结构。
{"title":"Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose","authors":"Jassem G. Mahdi , Hanaa M. Dawoud , Abigail J. Manning , Harvey F. Lieberman , David R. Kelly","doi":"10.1080/07328303.2019.1663204","DOIUrl":"10.1080/07328303.2019.1663204","url":null,"abstract":"<div><p>Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at <em>exo</em>-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose <strong>6</strong> produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose <strong>7</strong>. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound <strong>7</strong>.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 24-35"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1663204","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41768010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2019.1700996
Lang Lin , Jie Yang , Yan Yang , Hui Zhi , Xin Hu , Dongkun Chai , Yunjie Liu , Xiaojun Shen , Jie Wang , Yunqi Song , Aimei Zeng , Xinyu Li , Haibo Feng
In this study, the effects of phosphorylation of Radix Cyathula officinalis polysaccharide (RCPS) on its immunological properties were evaluated using broiler chickens immunized with Newcastle disease vaccine (NDV). The results suggested that phosphorylated RCPS (pRCPS) could enhance antibody titers against NDV vaccination, improve the indexes of thymus, the bursa of fabricius and spleen, and up-regulate IL-2, IL-4, IL-5, IL-6, IL-10, and IFN-γ. Overall, pRCPS could significantly improve cellular and humoral immune responses in broiler chickens immunized with NDV and thus represents a useful immunotherapeutic agent.
{"title":"Phosphorylation of Radix Cyathula officinalis polysaccharide improves its immune-enhancing activity","authors":"Lang Lin , Jie Yang , Yan Yang , Hui Zhi , Xin Hu , Dongkun Chai , Yunjie Liu , Xiaojun Shen , Jie Wang , Yunqi Song , Aimei Zeng , Xinyu Li , Haibo Feng","doi":"10.1080/07328303.2019.1700996","DOIUrl":"10.1080/07328303.2019.1700996","url":null,"abstract":"<div><p>In this study, the effects of phosphorylation of <em>Radix Cyathula officinalis</em> polysaccharide (RCPS) on its immunological properties were evaluated using broiler chickens immunized with Newcastle disease vaccine (NDV). The results suggested that phosphorylated RCPS (pRCPS) could enhance antibody titers against NDV vaccination, improve the indexes of thymus, the bursa of fabricius and spleen, and up-regulate IL-2, IL-4, IL-5, IL-6, IL-10, and IFN-γ. Overall, pRCPS could significantly improve cellular and humoral immune responses in broiler chickens immunized with NDV and thus represents a useful immunotherapeutic agent.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 50-62"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1700996","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42728827","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-01-01DOI: 10.1080/07328303.2021.1895195
Zhi-ling Cao , Cong Zhu , Wen-ying Wu , Dan-dan Zhu , Dong Qian , Jian Zhu , Tian-ge Chang , Mei Sheng , Xiu-li Yang , Wei-wei Liu
A facile method for the synthesis of a series of novel β-acylamino furans stating from renewable monosaccharide was achieved. Glucosamine hydrochloride was selectively N-acylated with acyl chlorides in methanol/triethylamine to yield N-acyl-d-glucosamines, which were subsequently converted into β-acylamino furans through dehydration and cyclization under microwave irradiation.
{"title":"Synthesis of β-acylamino furans from glucosamine","authors":"Zhi-ling Cao , Cong Zhu , Wen-ying Wu , Dan-dan Zhu , Dong Qian , Jian Zhu , Tian-ge Chang , Mei Sheng , Xiu-li Yang , Wei-wei Liu","doi":"10.1080/07328303.2021.1895195","DOIUrl":"10.1080/07328303.2021.1895195","url":null,"abstract":"<div><p>A facile method for the synthesis of a series of novel <em>β</em>-acylamino furans stating from renewable monosaccharide was achieved. Glucosamine hydrochloride was selectively <em>N</em>-acylated with acyl chlorides in methanol/triethylamine to yield <em>N</em>-acyl-<span>d</span><strong>-</strong>glucosamines, which were subsequently converted into <em>β</em>-acylamino furans through dehydration and cyclization under microwave irradiation.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 9","pages":"Pages 472-484"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1895195","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45135356","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}