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Synthesis and Solution Conformation of β ‐Hairpin Mimetics Utilizing a Template Derived from (2 S ,3 R ,4 R )‐Diaminoproline
Author(s) -
Pfeifer Marc E.,
Moehle Kerstin,
Linden Anthony,
Robinson John A.
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(20000216)83:2<444::aid-hlca444>3.0.co;2-r
Subject(s) - chemistry , combinatorial chemistry , peptide , sequence (biology) , stereochemistry , cyclic peptide , function (biology) , molecule , biochemistry , organic chemistry , evolutionary biology , biology
A novel template was synthesized for stabilizing β ‐hairpin conformations in cyclic peptide mimetics. The template is a diketopiperazine derived formally from L ‐aspartic acid and (2 S ,3 R ,4 R )‐diaminoproline, the latter being available by an efficient synthetic route from vitamin C. The template was incorporated by solid‐phase peptide synthesis into a cyclic loop mimetic containing the sequence (‐Ala‐Asn‐Pro‐Asn‐Ala‐Ala‐template‐). This mimetic was shown by NMR to adopt a stable β ‐hairpin conformation in (D 6 )DMSO solution. The template may prove to be generally useful for creating small‐molecule mimetics of hairpin loops on proteins of diverse function.