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首页> 外文期刊>Bulletin of the Chemical Society of Japan >Generation of an S-Peptide via an N-S Acyl Shift Reaction in a TFA Solution
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Generation of an S-Peptide via an N-S Acyl Shift Reaction in a TFA Solution

机译：在TFA溶液中通过N-S酰基转移反应生成S肽

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摘要

An N-S acyl shift reaction of thiol-containing peptides in a trifiuoroacetic acid (TFA) solution was confirmed by a combination of ~(13)CNMR spectroscopy,reversed-phase (RP) HPLC,and MS analyses.A model peptide containing a cysteine residue was transformed into an S-peptide in a TFA solution.The S-peptide was quickly transformed to the original peptide during RP-HPLC analysis even when an eluent that contained 0.1% TFA was used.A peptide that had an N-2-mercapto-4,5-dimethoxybenzyl (Dmmb) group was also transformed into an S-peptide,forming a thioester bond with the thiol of the Dmmb group by TFA treatment.The generated S-peptide was isolated by directly injecting the reaction mixture into a RP-FPLC and was readily converted to the corresponding 2-sulfoethyl thioester via an intermo-lecular thiol exchange reaction with sodium 2-mercaptoethanesulfonate.The 2-sulfoethyl peptide thioester is widely used as a building block in polypeptide synthesis.The N-S acyl shift reaction observed in peptides with or without an auxiliary group provides a new route for the preparation of peptide thioesters.
机译：通过〜（13）CNMR光谱，反相（RP）HPLC和MS分析相结合，证实了三氟乙酸（TFA）溶液中含巯基的肽的NS酰基转移反应。模型肽含有半胱氨酸残基在TFA溶液中将其转化为S肽。即使在使用含有0.1％TFA的洗脱液的情况下，RP-HPLC分析也将S肽快速转化为原始肽。还通过TFA处理将-4,5-二甲氧基苄基（Dmmb）基团转化为S-肽，与Dmmb基团的硫醇形成硫酯键，将反应混合物直接注入RP中分离出生成的S-肽-FPLC，并通过与2-巯基乙磺酸钠的分子间硫醇交换反应轻松转化为相应的2-磺基乙基硫酯.2-磺基乙基肽硫酯广泛用作多肽合成的基础，观察到NS酰基转移反应在p具有或不具有辅助基团的肽为制备肽硫酯提供了新途径。

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