Amino Acid Building Blocks for Efficient Fmoc Solid-Phase Synthesis of Peptides Adenylylated at Serine or Threonine

被引：7
|
作者：
Albers, Michael F. [1 ]
van Vliet, Bart [1 ]
Hedberg, Christian [1 ]
机构：
[1] Max Planck Inst Mol Physiol, Dept Biol Chem, D-44227 Dortmund, Germany
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 22期
关键词：
AMPYLATION; SYNTHETASE;
D O I：
10.1021/ol2024696
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first straightforward building block based (non-interassembly) synthesis of peptides containing adenylylated serine and threonine residues Is described. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The described Thr-AMP SPPS-building block has been employed in the synthesis of the Thr-adenylylated sequence of human GTPase CDC42 (Ac-SEYVP-T(AMP)-VFDNYGC-NH2). Further, we demonstrate proof-of-concept for the synthesis of an Ser-adenylylated peptide (Ac-GSGA-S(AMP)-AGSGC-NH2) from the corresponding adenylylated serine building block.
引用
收藏
页码：6014 / 6017
页数：4
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