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Synthesis and Evaluation of Enantiomeric Purity of Protected α-Amino and Peptide Aldehydes

✍ Scribed by Thomas Mindt; Urs Michel; F. Dick

Publisher
John Wiley and Sons
Year
1999
Tongue
German
Weight
125 KB
Volume
82
Category
Article
ISSN
0018-019X

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✦ Synopsis

The synthesis of enantiomerically pure Ac-Tyr-Val-Ala-Asp(O t Bu)-H dimethyl acetal ((S)-1) is reported, a protected tetrapeptide C-terminal aldehyde belonging to a class of potent, reversible inhibitors of cysteine proteases (e.g., interleukin-1b-converting enzyme (ICE), also called caspase-1). The coupling of the precursors Ac-Tyr-Val-Ala-OH ((S)-8) and H-Asp(O t Bu)-H dimethyl acetal ((S)-6) gave (S)-1 in a yield of 85%, with epimerization of `2% at the alanine and aspartic-acid residue. ( S )-6 itself was synthesized in four steps in an overall yield of 83% with an ee b 98%.

Helvetica Chimica Acta ± Vol. 82 (1999) Scheme 2 a) (R)-MTPA-Cl, pyridine/CCl 4 , 30 min, r.t., N,N-dimethylpropane-1,3-diamine [9]. Scheme 1 a) Isobutyl chloroformate/N-methylmorpholine/THF, NaBH 4 , À788. b) (COCl) 2 /DMSO/CH 2 Cl 2 , À458, i Pr 2 EtN. c) MeOH/TsOH/CH(OMe 3 ) 3 , r.t. d) H 2 , 10% Pd/C, MeOH, 48 h, r.t.

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