吗啉，固相肽合成中用于去除Fmoc的有力竞争者。

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

作者信息

Mthembu Sinenhlanhla N, Chakraborty Amit, Schönleber Ralph, Albericio Fernando, de la Torre Beatriz G

机构信息

Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa.

KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban, South Africa.

出版信息

J Pept Sci. 2024 Feb;30(2):e3538. doi: 10.1002/psc.3538. Epub 2023 Aug 23.

DOI:10.1002/psc.3538

PMID:37609959

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.

摘要

吗啉在绿色化学评分中得分为7.5且不属于受管制物质，在固相肽合成（SPPS）中可被视为用于脱除Fmoc的有力候选物。吗啉在二甲基甲酰胺（DMF）（50%-60%）中能有效地在SPPS中脱除Fmoc，将二酮哌嗪的形成降至最低，并且几乎能避免天冬酰胺的形成。作为概念验证，已使用50%吗啉的DMF溶液合成了生长抑素，其纯度与使用20%哌啶-DMF时相同。