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Tetrazolyl peptides and the tetrazole analogue of 3-aminonocardicinic acid

✍ Scribed by D.W Anderson; Malcolm M Campbell; Mohammed Malik

Book ID: 104222141
Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 176 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)88873-5

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✦ Synopsis

The synthesis of the tetrazole analogue of the @-lactam, 3-amirwnocardicinic acid, is described. Analogues of seryl p-hydroxy-phenylglycine were also prepared.

Replacement of the carboxyl group in biologically active compounds by the tetrazole group is undertaken because of the close similarity in pKa values, and the steric and electronic similarities.1

We therefore report the diastereoselective synthesis of the tetmzole (2). designed to mimic 3aminonocardicinic acid (l), the nucleus of the nocardicin family of antibiotics.' Tetrazole analogues (3) have been reported? but are more remote from the natural skeleton. A complementary study addresses the synthesis of the phosphonate analoguesP HzI)lloH H2;)2aoH

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