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Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis 水杨基硫代糖苷类化合物作为寡糖合成的无臭硫代糖苷替代品的反应性和立体选择性评价
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2021-01-01 DOI: 10.1080/07328303.2021.1921787
Hirofumi Dohi , Risa Sakurai , Manami Tamura , Ryota Komai , Yoshihiro Nishida

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.

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摘要本文中,o-(甲氧羰基)苯基硫糖苷[或(甲基)水杨酸基1-硫糖苷]被评估为无恶臭的硫糖苷替代品。邻甲氧羰基有望协助离去基团的离去。当N-碘代琥珀酰亚胺和三氟甲磺酸用作促进剂时,水杨酸基硫代糖苷表现出高的反应性和糖基化产率。这些硫代糖苷在二氯甲烷中的糖基化反应显示出与苯基硫代糖苷类似的反应性和立体选择性。在二氯甲烷中用全-O-苄基水杨酸基硫代糖苷进行的糖基化反应显示出1,2-顺式选择性,而在腈中进行的相同反应主要提供1,2-反式糖苷。相反,用全-O-苯甲酰基硫代糖苷进行糖基化仅提供1,2-反式糖苷。这些结果有力地表明,水杨酸基硫代糖苷可以作为苯基硫代糖苷的无恶臭替代品。图形摘要
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引用次数: 1
Purification, structural elucidation and immunostimulatory effect of a new protein-polysaccharide conjugate produced by Nervilia fordii 一种新的油桐蛋白-多糖结合物的纯化、结构分析及免疫刺激作用
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2021-01-01 DOI: 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.

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从油桐水提物中分离纯化了一种新的蛋白-多糖偶联物NFP-A4。发现NFP-A4的多糖链含有d -半乳糖、d -半乳糖、d -葡萄糖、l -阿拉伯糖、d -葡萄糖醛酸、l -鼠李糖和d -甘露糖。测定NFP-A4的蛋白质含量为12.83%,在丝氨酸和苏氨酸残基上通过o键结合到多糖链上。发现NFP-A4能显著激活巨噬细胞并诱导免疫调节反应。这些数据表明,NFP-A4是福氏弓形虫的主要生物活性成分,可能是其许多治疗特性的原因。下载:下载高清图片(370KB)下载:下载全尺寸图片
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引用次数: 0
Large-Scale Beard Extraction Enhances the Cosmetic Results of Scalp Hair Restoration in Advanced Androgenetic Alopecia in East Asian Men: A Retrospective Study. 大规模剔除胡须可提高东亚男性晚期雄激素性脱发患者头皮毛发修复的美容效果:一项回顾性研究。
IF 3.4 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-02-01 Epub Date: 2019-11-29 DOI: 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。
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引用次数: 0
Exploring substituent diversity of deoxynojirimycin–triazole hybrid iminosugars: Discovery of potent glucosidase inhibitors 探索脱氧诺吉霉素-三唑杂化亚糖的取代基多样性:发现有效的葡萄糖苷酶抑制剂
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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.

制备了一系列脱氧诺吉霉素-三唑杂化亚糖,并对其与葡萄糖苷酶的作用进行了研究。化合物10f (IC50 = 0.063±0.006 mM)对α-葡萄糖苷酶的抑制作用优于1-脱氧诺吉里霉素(IC50 = 0.155±0.015 mM)。此外,利用Lineweaver-Burk图分析酶抑制动力学表明,10f以竞争方式抑制α-葡萄糖苷酶。化合物10m对α-葡萄糖苷酶和β-葡萄糖苷酶有中等抑制作用。构效关系表明,苯基的引入和苯基环上4位取代基的性质对化合物的葡萄糖苷酶抑制效能有显著影响。
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引用次数: 3
A mild and convenient approach for selective acetonide cleavage involved in carbohydrate synthesis using PPA-SiO2 一种温和、方便的方法,用于选择性地裂解参与碳水化合物合成的丙酮
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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.

在这里,我们报道了一种高选择性、高效和快速的方法,用于选择性切割各种碳水化合物底物的二氧化硅负载的多磷酸(PPA-SiO2)。用PPA-SiO2在30 min内得到了相应的二醇,收率较高。总的来说,PPA-SiO2是一种有用的碳水化合物底物选择性裂解丙酮的催化剂,这可能扩大其在有机合成中的应用。
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引用次数: 1
Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate 丁基铵离子液体基质在基质辅助激光解吸/电离质谱检测与分析硫糖酸盐中的性能
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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.

本文比较了两种离子液体基质(ILMs)在质谱分析中不溶性和可溶性硫糖铝的性能。在α-氰基羟基肉桂酸(CHCAB)和2,5-二羟基苯甲酸(DHBB)丁铵盐的辅助下,进行了基质辅助激光解吸/电离质谱分析(MALDI MS)。CHCAB比DHBB具有更高的IE,但具有更好的光学性能。CHCAB更适合分析硫糖铝,尽管这两种化合物的分子离子只能在低强度下检测到。因此,ILMs的光学性质对提高MALDI质谱检测多磺酸寡糖的灵敏度至关重要。
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引用次数: 5
Chemical synthesis of the Pseudomonas aeruginosa O11 O-antigen trisaccharide based on neighboring electron-donating effect 基于邻近给电子效应的铜绿假单胞菌O11 o抗原三糖的化学合成
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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。
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引用次数: 4
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 2,3-异丙基-4-苯甲酰-1,6-无水-β- d -甘露糖立体选择性光溴化合成不稳定的4-苯甲酰-1,6-无水-β- d -甘露糖
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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 ,&nbsp;Hanaa M. Dawoud ,&nbsp;Abigail J. Manning ,&nbsp;Harvey F. Lieberman ,&nbsp;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}
引用次数: 0
Phosphorylation of Radix Cyathula officinalis polysaccharide improves its immune-enhancing activity 牛膝多糖的磷酸化提高了其免疫增强活性
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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.

本研究以新城疫疫苗(NDV)免疫肉鸡为试验对象,研究了Cyathula officinalis多糖(RCPS)磷酸化对其免疫特性的影响。结果表明,磷酸化的RCPS (pRCPS)可提高抗新城疫疫苗的抗体效价,改善胸腺、法氏囊和脾脏的各项指标,上调IL-2、IL-4、IL-5、IL-6、IL-10和IFN-γ的水平。综上所述,pRCPS能显著改善新城疫免疫肉鸡的细胞和体液免疫应答,是一种有用的免疫治疗剂。
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引用次数: 8
Synthesis of β-acylamino furans from glucosamine 葡萄糖胺合成β-酰基氨基呋喃
IF 1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2020-01-01 DOI: 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.

研究了以可再生单糖为原料合成一系列新型β-酰基氨基呋喃的简便方法。盐酸氨基葡萄糖在甲醇/三乙胺中与酰基氯选择性n -酰化,得到n -酰基-d-氨基葡萄糖,经微波辐照脱水和环化转化为β-酰基氨基呋喃。
{"title":"Synthesis of β-acylamino furans from glucosamine","authors":"Zhi-ling Cao ,&nbsp;Cong Zhu ,&nbsp;Wen-ying Wu ,&nbsp;Dan-dan Zhu ,&nbsp;Dong Qian ,&nbsp;Jian Zhu ,&nbsp;Tian-ge Chang ,&nbsp;Mei Sheng ,&nbsp;Xiu-li Yang ,&nbsp;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}
引用次数: 0
期刊
Journal of Carbohydrate Chemistry
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