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- Title
Synthesis and Solution Conformation of β-Hairpin Mimetics Utilizing a Template Derived from (2 S,3 R,4 R)-Diaminoproline.
- Authors
Pfeifer, Marc E.; Moehle, Kerstin; Linden, Anthony; Robinson, John A.
- Abstract
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 (D6)DMSO solution. The template may prove to be generally useful for creating small-molecule mimetics of hairpin loops on proteins of diverse function.
- Publication
Helvetica Chimica Acta, 2000, Vol 83, Issue 2, p444
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R