A Facile, Inexpensive and Scalable Route to Thiol-Protected α-Methyl 
Cysteine

Heather J. Johnston; Alison N. Hulme

doi:10.1055/s-0032-1318316

Synlett, Table of Contents

Synlett 2013; 24(5): 591-594
DOI: 10.1055/s-0032-1318316

letter

A Facile, Inexpensive and Scalable Route to Thiol-Protected α-Methyl Cysteine

Heather J. Johnston

School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh, EH9 3JJ, UK Fax: +44(131)6506453 Email: Alison.Hulme@ed.ac.uk

,

Alison N. Hulme*

School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh, EH9 3JJ, UK Fax: +44(131)6506453 Email: Alison.Hulme@ed.ac.uk

› Author Affiliations

Abstract

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Abstract

A facile, scalable synthesis of α-methyl cysteine with three alternate thiol protecting groups (trityl, allyl and tert-butyl) is described. The thiol-protected amino acids are obtained in six steps from l-cysteine ethyl ester and are ideally suited for a range of natural product and solid-phase peptide synthesis applications.

Key words

natural products - α-methyl cysteine - solid-phase peptide synthesis - camphorsultam auxiliary - P2-Et

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References

References and Notes
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For selected examples of RCM peptide stapling with the α-methyl all-carbon homologue, see:

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