389119-33-9Relevant academic research and scientific papers
Unexpected stability of the urea cis-trans isomer in urea-containing model pseudopeptides
Semetey, Vincent,Hemmerlin, Christine,Didierjean, Claude,Schaffner, Arnaud-Pierre,Giner, Ana Gimenez,Aubry, Andre,Briand, Jean-Paul,Marraud, Michel,Guichard, Gilles
, p. 3843 - 3845 (2001)
Equation Presented In contrast to the situation observed in the crystal state, the urea moiety in N-Boc-N-carbamoyl-gem-diaminoalkyl derivatives (single-residue ureidopeptides) 1-4 exclusively assumes a cis-trans conformation in solution. When R3/su
3,3-dichloro-1,2-diphenylcyclopropene (CPICL)-mediated synthesis of n α-protected amino acid azides and α-ureidopeptides
Panguluri, Nageswara Rao,Samarasimhareddy,Madhu,Sureshbabu, Vommina V.
, p. 1001 - 1005 (2014/05/06)
Rapid synthesis of acid azides via in situ generation of acid chlorides using CPICl as chlorinating agent from the corresponding Nα- protected amino acids is described. Also the conversion of acid azides into ureidopeptides through the Curtius rearrangement under ultrasonication is delineated. The mildness of the protocol renders the acid-sensitive substrates to afford the corresponding amino acid azides and ureidopeptides in good yields. Diphenylcyclopropenone has also been recovered from the reaction mixture and reused. Georg Thieme Verlag Stuttgart New York.
Efficient synthesis of O-succinimidyl-(tert-butoxycarbonylamino)methyl carbamates derived from α-amino acids accelerated by ultrasound: Application to the synthesis of ureidodipeptides
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Kantharaju
, p. 2168 - 2184 (2008/09/21)
The synthesis of O-succinimidyl-(tert-butoxycarbonylamino)methyl carbamates employing isocyanates made through the Curtius rearrangement of Boc-amino acid azides in the presence of N-hydroxysuccinimide under the influence of ultrasound is described. Copyright Taylor & Francis Group, LLC.
Pentafluorophenyl-(tert-butoxycarbonylamino) methylcarbamates: Synthesis, isolation and application to the synthesis of ureidopeptides
Sureshbabu, Vommina Venkata,Narendra,Kantharaju
, p. 920 - 926 (2008/12/23)
The one-pot synthesis of pentafluorophenyl-(tert-butoxycarbonylamino)methyl carbamates starting from N-Boc amino acids is described. Ultrasound mediated concomitant rearrangement and coupling reactions have resulted in the production of good yields of the active methyl carbamates. The carbamates have been employed as monomeric building blocks for the synthesis of dipeptidyl urea esters/acids. All the compounds obtained have been fully characterized by IR, 1H NMR, 13C NMR and mass spectroscopy.
Succinimidyl carbamate derivatives from N-protected α-amino acids and dipeptides-synthesis of ureidopeptides and oligourea/peptide hybrids
Fischer, Lucile,Semetey, Vincent,Lozano, Jose-Manuel,Schaffner, Arnaud-Pierre,Briand, Jean-Paul,Didierjean, Claude,Guichard, Gilles
, p. 2511 - 2525 (2008/03/13)
The preparation of succinimidyl (1-{[(alkyloxy)carbonyl]-amino}-1-X-methyl) carbamates (4) and succinimidyl [1-(acyl-amino)-1-X-methyl] carbamates (5) from a variety of N-Boc-, -Z- or -Fmoc-protected α-amino acids and dipeptides as well as the carbamate s
