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Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids

Lookup NU author(s): Herve Deboves, Professor Richard Jackson

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Abstract

The new N-Fmoc 3-iodoalanine tort-butyl ester derived organozinc reagent 1, obtained in 7 steps from optically pure L-serine. was coupled to a range of electrophiles under palladium catalysis to give substituted phenylalanines and 4-oxoamino acids in variable yields (21 59%). Transformation into the organocopper reagent 13 allowed coupling with allyl chloride and ethyl oxalyl chloride. Removal of the tort-butyl group gives Fmoc-protected amino acids (63-95%), suitable for use in automated solid phase peptide synthesis.

Publication metadata

Author(s): Deboves HJC, Montalbetti CAGN, Jackson RFW

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society, Perkin Transactions 1

Year: 2001

Issue: 16

Pages: 1876-1884

ISSN (print): 1472-7781

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/B103832J

DOI: 10.1039/b103832j

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