Synthesis of the conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids

Francis N Murigi; Gary S Nichol; Eugene A Mash

doi:10.1021/jo902438s

Synthesis of the conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids

J Org Chem. 2010 Feb 19;75(4):1293-6. doi: 10.1021/jo902438s.

Authors

Francis N Murigi¹, Gary S Nichol, Eugene A Mash

Affiliation

¹ Department of Chemistry and Biochemistry, University of Arizona, Tucson, Arizona 85721-0041, USA.

PMID: 20095557
DOI: 10.1021/jo902438s

Abstract

The conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids, were prepared by chromatographic separation of diastereomeric dipeptide derivatives formed from N-Boc-L-phenylalanine. Absolute configurations were assigned by X-ray crystallographic analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, Gel
Chromatography, High Pressure Liquid
Crystallography, X-Ray
Dipeptides / chemistry*
Indans / chemical synthesis*
Indans / chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Phenylalanine / chemistry*
Stereoisomerism
Tyrosine / chemical synthesis*
Tyrosine / chemistry

Substances

Dipeptides
Indans
Tyrosine
Phenylalanine