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Efficient Synthesis of Differentially Protected ( S , S )‐2,7‐ Diaminooctanedioic Acid, the Dicarba Analogue of Cystine
Author(s) -
Lange Meinolf,
Fischer Peter M.
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4
Subject(s) - chemistry , phenacyl , hydrolysis , ether , peptide , acid hydrolysis , amino acid , cystine , organic chemistry , combinatorial chemistry , stereochemistry , biochemistry , cysteine , enzyme
Convenient preparative syntheses of differentially protected forms of ( S , S )‐2,7‐diaminooctanedioic acid ( 2 ), suitable for application in peptide chemistry, are described. The key compound, the di‐Cbz‐protected phenacyl monoester 7a (Cbz=[(benzyloxy)carbonyl]), was obtained by means of Schöllkopf bis‐lactim ether methodology and optimized monoesterification procedures. Selective amino deprotection at the non‐esterified amino‐acid function of 7a by dichloromethyl‐methyl‐ether‐induced ` N ‐carboxyanhydride' formation, and hydrolysis permitted access to the Boc/Cbz‐ and Fmoc/Cbz‐protected monophenacyl esters 11a and 11b , as well as to the fully orthogonally protected Fmoc/Boc monophenacyl ester 12 (Boc=( tert ‐butoxy)carbonyl, Fmoc=(9 H ‐fluoren‐9‐ylmethoxy)carbonyl).