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 |
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Format: | Artikel |
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 |
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ISSN: | 1573-3149 1573-3904 |
DOI: | 10.1007/s10989-014-9448-2 |