Solid-supported synthesis of a peptide beta-turn mimetic

A Golebiowski; S R Klopfenstein; X Shao; J J Chen; A O Colson; A L Grieb; A F Russell

doi:10.1021/ol006145s

Solid-supported synthesis of a peptide beta-turn mimetic

Org Lett. 2000 Aug 24;2(17):2615-7. doi: 10.1021/ol006145s.

Authors

A Golebiowski¹, S R Klopfenstein, X Shao, J J Chen, A O Colson, A L Grieb, A F Russell

Affiliation

¹ Procter & Gamble Pharmaceuticals, Combinatorial Chemistry Group, Health Care Research Center, Mason, Ohio 45040-8006, USA. [email protected]

PMID: 10990410
DOI: 10.1021/ol006145s

Abstract

[structure: see text]The solid-supported synthesis of a bicyclic diketopiperazine, a potential peptide beta-turn mimetic, is described. The Ugi reaction between the resin ester of alpha-N-Boc-diaminopropionic acid (an amine input), alpha-bromo acid, aldehyde, and isocyanide is the key step in the proposed protocol.

MeSH terms

Chromatography, High Pressure Liquid
Indicators and Reagents
Models, Molecular
Peptides / chemical synthesis*
Peptides / chemistry
Piperazines / chemistry
Protein Structure, Secondary
Spectrophotometry, Ultraviolet
Stereoisomerism
beta-Alanine / analogs & derivatives
beta-Alanine / chemistry

Substances

Indicators and Reagents
Peptides
Piperazines
beta-Alanine
2,3-diaminopropionic acid