多肽合成用的树脂,你知道多少?
一、 Wang-Resin 王树脂
Wang resin is the most widely used resin for SPOS. As a standard support it can be used for the solid phase immobilization of acids and phenols for SPOS. The ester linkage may be achieved, which has good stability to a variety of reaction conditions, but can be readily removed with the moderate acid treatment, generally with TFA, For the immobilization of amines, Wang resin also can be readily converted into solid phase equivalents of standard urethine-based protecting groups by reaction with phosgene or activated carbonates, such as carbonyl diimidaiole or bis(p-nitrophenyl)-carbonate.
在多肽的合成中,与Wang Resin相连接的氨基酸,通常除去Pro、His、Cys。切割后,C端为羧基形式。
A extremely acid-labile resin for preparing peptides and partially protected peptide fragments by the Fmoc strategy. This resin is ideal for use in the preparation of peptides containing C-terminal Cys, His, Met, Tyr and Pro residues. Cleavage for protected peptides from this matrix can be effected by treatment with AcOH/TFE/DCM,0.5% TFA or HFIP. Fully deprotected peptides can also be obtained by cleaving with 95% TFA in the usual manner.
常用名有:2-CTC Resin、二氯树脂。
特点:此树脂对酸非常敏感,通常0.5%TFA就可以将氨基酸从树脂上脱落。
用途:基本上所有的氨基酸都可以连接到二氯树脂上,通常C端为Cys、Pro、His时都会选择使用二氯树脂,切割后,C端为羧基形式。
三、Aminomethyl resin, AM resin, AM树脂
The Aminomethyl resin is one of the most widely used functionalized supports for solid-phase synthesis. Many supports can be made by acylating this resin with carboxylic acid-containing linkers using standard methods of amide bond formation to furnish supports for SPOS. It is also used as a scavenger resin in solution phase synthesis to remove excess acids, alkylating agents and other electrophiles.
一种常见的实现C端酰胺化的功能载体,在C端第一个氨基酸和AM树脂之间,需要加入一种含羧基的交联剂,如Fmoc-Linker-OH (CAS:145069-56-3),以实现C端酰胺化。
Fmoc-Linker-AM Resin也叫做Rink Amide-AM Resin
其结构如下
四、4-methylbenzhydrylamine Resin, MBHA resin
4-methylbenzhydrylamine Hydrochloride Salt Resin (MBHA resin)
MBHA resin is used in the synthesis of peptide amide by Boc chemistry. This support is more acid sensitive than BHA resin, and thus allow release of the product to be effected with HF or TFMSA under less drastic conditions.
也是一种常见的实现C端酰胺化的功能载体。在C端第一个氨基酸和MBHA树脂之间,需要加入一种含羧基的交联剂,如Fmoc-Linker-OH (CAS:145069-56-3),以实现C端酰胺化。
Fmoc-Linker-MBHA Resin也叫做Rink Amide-MBHA Resin
其结构如下:
下期介绍这几种树脂与C端第一个氨基酸的连接方法,含具体操作步骤和试剂比例。
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