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A Unified Approach to Access N ‐Acyl Sulfonamide Tethered Peptide Conjugates
Author(s) -
Sagar Nagamangala Ramachandra,
Durgamma Suram,
Srinivasulu Chinthaginjala,
Basavaprabhu Hosamani,
Sureshbabu Vommina Venkata
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901024
Subject(s) - sulfonamide , peptidomimetic , chemistry , conjugate , aryl , combinatorial chemistry , peptide , sulfonyl , intramolecular force , amino acid , acylation , stereochemistry , alkyl , organic chemistry , catalysis , biochemistry , mathematical analysis , mathematics
Herein we demonstrate a chemoselective reaction of N β ‐protected amino alkyl sulfonyl azides with in situ generated N α ‐protected amino acid selenocarboxylates via step wise intramolecular cyclization followed by decomposition to obtain N‐acyl sulfonamide tethered peptidyl conjugates. The protocol offers the synthesis of orthogonally protected N‐acyl sulfonamide tethered peptidomimetics under simple and mild reaction conditions employing commercially available amino acids in presence of NaBH 2 Se 3 as a selenating agent. Also, the synthesis of N‐acyl sulfonamide tethered amino acid and aryl conjugates were accomplished as an extension of the above strategy.