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固定化偶联试剂:酰胺/肽的合成

Immobilized coupling reagents: synthesis of amides/peptides.

作者信息

Cherkupally Prabhakar, Ramesh Suhas, de la Torre Beatriz G, Govender Thavendran, Kruger Hendrik G, Albericio Fernando

机构信息

Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal , Durban 4001, South Africa.

出版信息

ACS Comb Sci. 2014 Nov 10;16(11):579-601. doi: 10.1021/co500126y. Epub 2014 Oct 24.

Abstract

The primary idea of using immobilized reagents in organic synthetic chemistry is to simplify the downstream process, product workup and isolation, and therefore avoiding time-consuming and expensive chromatographic separations, which are intrinsic to every synthetic process. Numerous polymer-bounded reagents are commercially available and applicable to almost all kinds of synthetic chemistry conversions. Herein, we have covered all known supported-coupling reagents and bases which have had a great impact in amide/peptide bond formation. These coupling reagents have been used for the activation of a carboxyl moiety; thus generating an active acylating species that is ready to couple with an amine nucleophile liberating the amide/peptide and polymeric support which can be regenerated for reuse. This also addresses a large variety of anchored coupling reagents, additives, and bases that have only been employed in amide/peptide syntheses during the last six decades.

摘要

在有机合成化学中使用固定化试剂的主要目的是简化下游过程、产物后处理和分离,从而避免耗时且昂贵的色谱分离,而色谱分离是每个合成过程所固有的。许多聚合物负载的试剂在市场上都有销售,并且几乎适用于所有类型的合成化学转化。在此,我们涵盖了所有已知的在酰胺/肽键形成中具有重大影响的负载型偶联试剂和碱。这些偶联试剂已用于羧基部分的活化;从而生成一种活性酰化物种,该物种准备好与胺亲核试剂偶联,释放出酰胺/肽和可再生成以供重复使用的聚合物载体。这也涉及到在过去六十年中仅用于酰胺/肽合成的各种锚定偶联试剂、添加剂和碱。

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