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Stereospecific Synthesis of a Novel Farnesyl Protein Transferase Inhibitor, Valinoctin A and Its Analogues

M Tsuda, Y Muraoka, T Takeuchi, R Sekizawa, K Umezawa

J Antibiot (Tokyo). 1996 Oct;49(10):1031-5.

PMID: 8968397

Abstract:

(2S,3R)-3-Amino-2-hydroxyoctanoic acid was synthesized by Curtius rearrangement of an azide derivative of (S)-malic acid. Total syntheses of valinoctin A and its analogues were achieved by a coupling of (2S, 3R)-3-amino-2-hydroxyoctanoic acid moiety with L-valine or several other amino acids moieties. 2S configuration of 3-amino-2-hydroxyoctanoic acid moiety was found to be important for the inhibitory activity and the L-valine moiety of valinoctin A was exchangeable with other L-amino acids.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP617732 (±)-2-Hydroxyoctanoic acid (±)-2-Hydroxyoctanoic acid 617-73-2 Price
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