Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 11, Pages 2307-2317Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob07172j
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Funding
- MIUR
- Fondazione del Monte di Bologna e Ravenna [FC 11/2011]
- Italian Minister for Foreign Affairs
- Fondazione per la Ricerca sulla Fibrosi Cistica, Verona
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The reaction of sulfonyl peptides containing L- or D-configured Ser or Thr with bis(succinimidyl) carbonate in the presence of a catalytic amount of a base affords, in solution or in the solid phase, the corresponding peptides with one or two, consecutive or alternate oxazolidin-2-ones (Oxd). The Oxd ring can be regarded to as a pseudo-Pro with an exclusively trans conformation of the preceding peptide bond; homochiral Oxd-containing peptides adopt extended conformations, while the presence of a D-configured Oxd favours folded conformations.
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