Tetrahedron Letters, volume 34, issue 3, pages 381-384
A Convenient synthesis of the, conformationally constrained amino acid 5,5-dimethylproline
Victoria W Magaard
1
,
Robert M Sanchez
1
,
JOHN W. BEAN
2
,
Michael J. Moore
1
1
Department of Peptidomimetic Research SmithKline Beecham Pharmaceuticals, King of Prussia, PA, 19406, USA
|
2
Department of Pysical and Structural Chemistry SmithKline Beecham Pharmaceuticals, King of Prussia, PA, 19406, USA
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Publication type: Journal Article
Publication date: 1993-01-01
Journal:
Tetrahedron Letters
scimago Q3
wos Q3
SJR: 0.323
CiteScore: 3.5
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
5,5-Dimethylproline was designed to induce a cis -peptide bond when incorporated into peptides. In a model dipeptide, it exists 90% as the cis isomer. A convenient synthesis of Boc- DL -5,5-dimethylproline methyl ester is described. This conformationally-constrained amino acid may be expected to exist predominantly in the cis peptide bond isomer when into peptides. The peptide bond in the model peptide Boc-Phe-Me 2 Pro-OMe is shown to be 90% in the cis isomer.
Found
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