Solid-phase synthesis of N,N′-unsymmetrically substituted ureas: application to the synthesis of carbaza peptides
| Autor: | Pascal Dalbon, Jean-Paul Briand, David Limal, Michel Jolivet, Vincent Semetey |
|---|---|
| Přispěvatelé: | Institut de Biologie Moléculaire et Cellulaire [Strasbourg] (IBMC) |
| Rok vydání: | 1999 |
| Předmět: |
chemistry.chemical_classification
Triphosgene 010405 organic chemistry Organic Chemistry Peptide 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Solid-phase synthesis chemistry Reagent Drug Discovery Urea [CHIM]Chemical Sciences Moiety ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Tetrahedron Letters Tetrahedron Letters, Elsevier, 1999, 40 (14), pp.2749-2752. ⟨10.1016/S0040-4039(99)00288-9⟩ |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/s0040-4039(99)00288-9 |
| Popis: | The synthesis of Boc- or Fmoc-monoprotected propylenediamine derivatives is reported starting from N-protected α-amino acids. The introduction of these building blocks on solid support via the formation of a urea moiety leads to a new pseudopeptide family (CαCH2CH2Nα(R)CONHCα). Two carbonylating reagents, i.e N,N′-carbonyldiimidazole and triphosgene, as well as different coupling procedures, have been tested to optimize the Boc and Fmoc solid-phase synthesis of a model peptide incorporating this isosteric replacement. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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