Journal
CHEMISTRYSELECT
Volume 4, Issue 20, Pages 6408-6413Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201901024
Keywords
N-Acyl sulfonamide; N-alpha-protected amino selenocarboxylate; N-beta-protected amino alkyl sulfonyl azides; peptide conjugates
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Funding
- Science and Engineering Research Board (SERB), Govt. of India [EMR/2016/002432]
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Herein we demonstrate a chemoselective reaction of N-beta-protected amino alkyl sulfonyl azides with in situ generated N-alpha-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 NaBH2Se3 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.
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