SYNTHESIS OF PROTECTED OMEGA-MERCAPTO AMINO-ACIDS - PRECURSORS FOR INCORPORATION OF ELONGATED CYSTEINES INTO PEPTIDES

Authors
LUNDQUIST JT BULLESBACH EE DIX TA
Citation
Jt. Lundquist et al., SYNTHESIS OF PROTECTED OMEGA-MERCAPTO AMINO-ACIDS - PRECURSORS FOR INCORPORATION OF ELONGATED CYSTEINES INTO PEPTIDES, Tetrahedron : asymmetry, 9(15), 1998, pp. 2739-2743
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
15
Year of publication
1998
Pages
2739 - 2743
Database
ISI
SICI code
0957-4166(1998)9:15<2739:SOPOA->2.0.ZU;2-T
Abstract
A series of protected omega-mercapto amino acids with side-chain lengt hs ranging from 3-5 methylene units has been synthesized via nucleophi lic substitution of omega-bromo-alpha-azido acids by 4-methoxy-alpha-t oluenethiol followed by reduction of the azido functionality with SnCl 2. These enantiomerically pure protected cysteine analogues can be use d to optimize the length of disulfide connections in cyclically constr ained peptide pharmacophores. (C) 1998 Elsevier Science Ltd. All right s reserved.