固相合成对硝基苯侧链保护。

Peptide research Pub Date : 1995-11-01
M D Hocker, C G Caldwell, R W Macsata, M H Lyttle
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引用次数: 0

摘要

描述了一种固相支持的肽合成(SPPS)策略,使用对硝基苯(pNB)酯、硫醚和氨基甲酸酯进行侧链保护。以Wang聚苯乙烯树脂为原料,采用标准的Fmoc方法合成了赖氨酸、半胱氨酸、谷氨酸和天冬氨酸对硝基苯侧链保护氨基酸,并将其加入到四聚体的合成中。以DMF、SnCl2、苯酚和HOAc为溶剂,在弱酸性还原条件下对树脂进行脱保护。与pNB保护基团脱保护有关的黄色副产物然后用亚磺酸苯溶液在DMF中处理去除。该方法已成功地扩展到合成具有多个pNB保护基团的肽。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
p-Nitrobenzyl side-chain protection for solid-phase synthesis.

A solid-phase supported peptide synthesis (SPPS) strategy using p-nitrobenzyl (pNB) esters, thioethers and carbamates for side-chain protection is described. The synthesis of Fmoc p-nitrobenzyl side-chain protected amino acids of lysine, cysteine, glutamic acid and aspartic acid are synthesized and incorporated into the synthesis of tetramers by standard Fmoc methodology using Wang polystyrene resins. Deprotection is carried out on resin in mildly acidic reducing conditions, using a solution of DMF, SnCl2, phenol and HOAc. The yellow by-products associated with the deprotection of the pNB protecting group are then removed by treatment with a solution of benzene sulfinic acid in DMF. The methodology is successfully extended in the synthesis of a peptide with multiple pNB protecting groups.

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