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A Facile Synthesis of 1,5-Disubstituted Tetrazole Peptidomimetics by Desulfurization/Electrocyclization of Thiopeptides

Prabhu, Girish and Nagendra, Govindappa and Sagar, NR and Pal, Rumpa and Row, Tayur N Guru and Sureshbabu, Vommina V (2016) A Facile Synthesis of 1,5-Disubstituted Tetrazole Peptidomimetics by Desulfurization/Electrocyclization of Thiopeptides. In: ASIAN JOURNAL OF ORGANIC CHEMISTRY, 5 (1). pp. 127-137.

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Official URL: http://dx.doi.org/10.1002/ajoc.201500384

Abstract

The cis-amide bond isostere, 1,5-disubstituted tetrazole,has been introduced in the peptide backbone by a simple route starting from the thiopeptide. The desired 1,5-disubstituted tetrazole peptidomimetics were synthesized by the desulfurization of thiopeptides by using HgCl2 in the presence of NaN3/TEA in DMF in good yields. Various other thiophilic reagents including hypervalent iodine reagents failed to deliver the tetrazole product with the exception of CBr4/PPh3, which resulted in moderate yields. The advantage of the present protocol over previous methods has been demonstrated by the selective insertion of tetrazole into peptide-thiopeptide hybrids. Also, the protocol is compatible with commonly employed urethane protecting groups (Fmoc, Boc, and Cbz) in peptide chemistry. Thiopeptide Boc-Pro-CSNH]-Val-OMe (2i) and two tetrazole peptidomimetics Cbz-Ala-CN4]-Phe-OMe (3d) and Boc-Pro-CN4]-Val-OMe (3i) were obtained as single crystals and their molecular structures have been confirmed by X-ray crystallography.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMAN
Keywords: 1,5-disubstituted tetrazoles; cis-amides; peptides; peptidomimetics; thiopeptides
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Id for Latest eprints
Date Deposited: 04 Mar 2016 07:49
Last Modified: 04 Mar 2016 07:49
URI: http://eprints.iisc.ac.in/id/eprint/53320

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