One-Pot Synthesis of New Class of Dithiocarbonate-Tethered Peptidomimetics

A simple and an efficient one-pot protocol for the synthesis of a new class of dithiocarbonate-tethered peptidomimetics and neo-glycosylated amino acids have been developed. This synthetic process involves in situ generation of a dithiocarbonate salt from the N α -protected aminol substrate by react...

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Veröffentlicht in:International journal of peptide research and therapeutics 2015-06, Vol.21 (2), p.195-203
Hauptverfasser: Krishnamurthy, Muniyappa, Basavaprabhu, Sureshbabu, Vommina V.
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Sprache:eng
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Zusammenfassung:A simple and an efficient one-pot protocol for the synthesis of a new class of dithiocarbonate-tethered peptidomimetics and neo-glycosylated amino acids have been developed. This synthetic process involves in situ generation of a dithiocarbonate salt from the N α -protected aminol substrate by reacting with CS 2 followed by addition of bromo amino acid/sugar bromide to form the desired products. Amino acids with simple as well as bifunctional side chains were employed to obtain dithiocarbonate-tethered peptidomimetics in good yields. Further, the protocol was extended for the synthesis of N , N′ -orthogonally protected dithiocarbonate-tethered peptidomimetics. Graphical Abstract
ISSN:1573-3149
1573-3904
DOI:10.1007/s10989-014-9448-2