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Improved synthesis of (S)-N-Boc-5-oxaproline for protein synthesis with the α-ketoacid-hydroxylamine (KAHA) ligation.

Abstract：

:We describe a new route for the synthesis of (S)-N-Boc-5-oxaproline. This building block is a key element for the chemical synthesis of proteins with the α-ketoacid-hydroxylamine (KAHA) ligation. The new synthetic pathway to the enantiopure oxaproline is based on a chiral amine mediated enantioselective conjugate addition of a hydroxylamine to trans-4-oxo-2-butenoate. This route is practical, scalable and economical and provides decagram amounts of material for protein synthesis and conversion to other protected forms of (S)-oxaproline.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Murar CE,Harmand TJ,Bode JW

doi

10.1016/j.bmc.2017.06.019

subject

Has Abstract

pub_date

2017-09-15 00:00:00

pages

4996-5001

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(17)30774-5

journal_volume

25

pub_type

杂志文章

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