329309-01-5Relevant academic research and scientific papers
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.
Application of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) for the synthesis of acid azides
Naik, Shankar A.,Lalithamba,Sureshbabu, Vommina V.
experimental part, p. 103 - 109 (2011/04/15)
Conversion of acids to acyl azides using peptide coupling agent TBTU has been demonstrated. The procedure is simple and applicable to a range of carboxylic acids under mild reaction conditions. The protocol is extended to the synthesis of urethane protect
Characterization of Nα-Fmoc-protected ureidopeptides by electrospray ionization tandem mass spectrometry (ESI-MS/MS): Differentiation of positional isomers
Ramesh,Raju,Srinivas,Sureshbabu,Narendra,Vasantha
experimental part, p. 1461 - 1472 (2011/09/15)
Four pairs of positional isomers of ureidopeptides, FmocNH-CH(R 1)-φ(NH-CO-NH)-CH(R2)-OY and FmocNH-CH(R 2)-φ(NH-CO-NH)-CH(R1)-OY (Fmoc = [(9-fluorenyl methyl)oxy]carbonyl; R1 = H, alkyl; R2/sub
New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: Application of peptide coupling agents EDC and HBTU
Sureshbabu, Vommina V.,Lalithamba,Narendra,Hemantha
experimental part, p. 835 - 840 (2010/06/20)
Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved. The Royal Society of Chemistry 2010.
Facile one step synthesis of acyl azides and Nα-Fmoc/Boc/Z protected amino acid azides employing benzotriazole-1-yl-oxy-tris- (dimethylamino)-phosphonium hexafluorophosphate (BOP)
Vasantha,Sureshbabu, Vommina V.
experimental part, p. 812 - 817 (2011/01/04)
A simple route for the preparation of acyl azides from the corresponding carboxylic acids employing the peptide-coupling agent BOP is described. The procedure is simple, clean and high yielding. The chemistry is also extended to the preparation of several urethane protected amino acid azides (eight examples) as well.
Synthesis of Nα-protected amino acid-derived selenocarbamates employing isocyanates as key intermediates
Sureshbabu, Vommina V.,Naik, Shankar A.
experimental part, p. 2676 - 2685 (2010/11/03)
A simple protocol for the synthesis of Nα-urethane-protected N-alkyl-Se-alkyl selenocarbamate derivatives of amino acids has been described. The reaction of Nα-urethane-protected amino alkyl isocyanates with selenating agent LiAlHSeH and subsequent coupli
An efficient conversion of the carboxylic group of N-Fmoc α-amino acids/peptide acids into N-formamides employing isocyanates as key intermediates
Sudarshan,Narendra,Hemantha,Sureshbabu, Vommina V.
, p. 9804 - 9807 (2008/03/27)
(Chemical Equation Presented) Reaction of 96% formic acid with isocyanates derived from N-Fmoc α-amino acids/peptide acids catalyzed by DMAP has yielded a new class of stable formamides as crystalline solids which have been characterized by IR, 1/su
Synthesis of retro-inverso peptides employing isocyanates of Nα-Fmoc-amino acids/peptide acids catalyzed by DMAP
Venkataramanarao, Rao,Sureshbabu, Vommina V.
, p. 9139 - 9141 (2007/10/03)
The Goldschmidt-Wick type reaction between isocyanates of Nα-Fmoc-amino acids/peptide acids and Nα-Boc-/Z-/Bsmoc-amino acids catalyzed by DMAP leads to the incorporation of a reversed peptide bond. It was found to be a simple, effici
Fmoc-amino acid azides in peptide synthesis
Vasanthakumar, Ganga-Ramu,Ananda, Kuppanna,Suresh Babu, Vommina V
, p. 1733 - 1735 (2007/10/03)
Fmoc-amino acid azides can be prepared from the corresponding acid chlorides and sodium azide. All the compounds made have been obtained as solids in good yield and purity. They are found to be shelf stable at room temperature for longer periods. Their storage at room temperature does not lead to the formation of isocyanates. Employing them as coupling agents, the synthesis of a few dipeptides is described.
(Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid azides: Synthesis, isolation, characterisation, stability and application to synthesis of peptides
Babu, Vommina V. Suresh,Ananda, Kuppanna,Vasanthakumar, Ganga-Ramu
, p. 4328 - 4331 (2007/10/03)
The synthesis of Fmoc amino acid azides starting from the corresponding protected amino acid and sodium azide (NaN3) by the mixed anhydride method using isobutoxycarbonyl chloride (IBC-Cl) or by the acid chloride method is described. Isolated as crystalli
