Morpholine, a strong contender for Fmoc removal in solid-phase peptide synthesis

IF 1.8 4区 生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Journal of Peptide Science Pub Date : 2023-08-23 DOI:10.1002/psc.3538
Sinenhlanhla N. Mthembu, Amit Chakraborty, Ralph Schönleber, Fernando Albericio, Beatriz G. de la Torre
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Abstract

Morpholine, which scores 7.5 in terms of greenness and is not a regulated substance, could be considered a strong contender for Fmoc removal in solid-phase peptide synthesis (SPPS). Morpholine in dimethylformamide (DMF) (50%–60%) efficiently removes Fmoc in SPPS, minimizes the formation of diketopiperazine, and almost avoids the aspartimide formation. As a proof of concept, somatostatin has been synthesized using 50% morpholine in DMF with the same purity as when using 20% piperidine–DMF.

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吗啉,固相肽合成中去除 Fmoc 的有力竞争者。
吗啉的绿色程度为 7.5 分,而且不属于管制物质,因此可被视为固相肽合成(SPPS)中去除 Fmoc 的有力竞争者。二甲基甲酰胺(DMF)中的吗啉(50%-60%)能有效去除 SPPS 中的 Fmoc,最大程度地减少二酮哌嗪的形成,并几乎避免了天冬酰亚胺的形成。作为概念验证,在 DMF 中使用 50% 吗啉合成的体生长抑素的纯度与使用 20% 哌啶-DMF 合成的体生长抑素的纯度相同。
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来源期刊
Journal of Peptide Science
Journal of Peptide Science 生物-分析化学
CiteScore
3.40
自引率
4.80%
发文量
83
审稿时长
1.7 months
期刊介绍: The official Journal of the European Peptide Society EPS The Journal of Peptide Science is a cooperative venture of John Wiley & Sons, Ltd and the European Peptide Society, undertaken for the advancement of international peptide science by the publication of original research results and reviews. The Journal of Peptide Science publishes three types of articles: Research Articles, Rapid Communications and Reviews. The scope of the Journal embraces the whole range of peptide chemistry and biology: the isolation, characterisation, synthesis properties (chemical, physical, conformational, pharmacological, endocrine and immunological) and applications of natural peptides; studies of their analogues, including peptidomimetics; peptide antibiotics and other peptide-derived complex natural products; peptide and peptide-related drug design and development; peptide materials and nanomaterials science; combinatorial peptide research; the chemical synthesis of proteins; and methodological advances in all these areas. The spectrum of interests is well illustrated by the published proceedings of the regular international Symposia of the European, American, Japanese, Australian, Chinese and Indian Peptide Societies.
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