270575-68-3Relevant academic research and scientific papers
Synthesis of β-lactam peptidomimetics through Ugi MCR: First application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs
Vishwanatha,Narendra,Sureshbabu, Vommina V.
scheme or table, p. 5620 - 5624 (2011/11/06)
Chiral Nβ-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized β-lactam peptidomimetics with l-aspartic acid α-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities.
Cyanogen bromide as dehydrosulfurizing agent for the synthesis of N β-Fmoc-amino alkyl isonitriles from Nβ-Fmoc- amino alkyl thioformamides
Vishwanatha,Hemantha,Sureshbabu
scheme or table, p. 1096 - 1100 (2010/06/20)
Synthetically useful Nβ-Fmoc amino alkyl isonitriles are prepared conveniently from Nβ-Fmoc amino alkyl thioformamides via a cyanogen bromide mediated dehydrosulfurization. The reaction is fast, clean, and yields are good. Georg Thieme Verlag Stuttgart - New York.
Chiral N-Fmoc-β-amino alkyl isonitriles derived from amino acids: First synthesis and application in 1-substituted tetrazole synthesis
Sureshbabu, Vommina V.,Narendra,Nagendra
supporting information; experimental part, p. 153 - 157 (2009/04/07)
(Chemical Equation Presented) A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-β-amino acids into an isocyano group has resulted in a new class of N-uretha
Helix-forming oligoureas: Temperature-dependent NMR, structure determination, and circular dichroism of a nonamer with functionalized side chains
Hemmerlin, Christine,Marraud, Michel,Rognan, Didier,Graff, Roland,Semetey, Vincent,Briand, Jean-Paul,Guichard, Gilles
, p. 3692 - 3711 (2007/10/03)
To further investigate the degree of structural homology between γ-peptides A and N,N′-linked oligoureas B, we prepared oligourea nonamer 2 containing Ala, Val, Leu, Phe, Tyr and Lys side chains. Oligomer 2 was synthesized on solid support from activated monomers, i.e., from enantiomerically pure succinimidyl {2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl}carbamates 3a-f that are further substituted at C(2) of the ethyl moiety. These precursors were conveniently prepared from N-Fmoc-protected β3-amino acids with corresponding side chains. Detailed NMR studies (DQF-COSY, TOCSY, and ROESY) in (D5)pyridine revealed that 2 adopts a regular (P)-2.5 helical secondary structure very similar to that previously determined for oligourea heptamer 1 and closely related to the (P)-2.614 helix of γ-peptides. Temperature-dependent NMR further demonstrated the conformational homogeneity and remarkable stability of the structure of 2 in pyridine. The CD spectrum of 2 (0.2 mm) was recorded in MeOH with the aim to gain more information about the conformation of oligoureas. In contrast to 2.6-helical γ-peptides, which display only a weak or no Cotton effect, oligourea 2 exhibits an intense positive Cotton effect at ca. 203 nm ([O] = +373000 deg cm2 dmol-1) that decreases only slowly upon increasing the temperature.
Solid phase synthesis of oligoureas using O-succinimidyl-(9H-fluoren-9- ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers
Guichard, Gilles,Semetey, Vincent,Rodriguez, Marc,Briand, Jean-Paul
, p. 1553 - 1557 (2007/10/03)
An efficient stepwise synthesis of oligoureas (up to the nonamer) on solid support using O-succinimidyl-(9H-fluoren-9- ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers is described. These building blocks were readily prepared starting from N-Fmoc- protected β3-amino acids via Curtius rearrangement of the corresponding acyl azides and treatment of the resulting isocyanate with N- hydroxysuccinimide. (C) 2000 Elsevier Science Ltd.
