Stereoselective synthesis of natural and non-natural thomsen-nouveau antigens and hydrazide derivatives
A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to α- or β-anomers in excellent yields (72-96%) and selectivity (~100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.
Shaik, Ahmad Ali,Nishat, Sharmeen,Andreana, Peter R.
p. 2582 - 2585
(2015/06/16)
Synthesis of δ-(L-α-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D- allothreonine a substrate for isopenicillin-N synthase and its O-Methyl-D- threonine epimer
The paper describes the synthesis of two epimeric tripeptides δ-(L-α- aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and δ-(L-α- aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enz
Petursson, Sigthor,Baldwin, Jack E.
p. 6001 - 6010
(2007/10/03)
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