938464-44-9Relevant academic research and scientific papers
Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
Surcshbabu, Vommina V.,Sudarshan,Chennakrishnareddy
experimental part, p. 574 - 579 (2009/12/06)
The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
HOBt·DCHA-mediated synthesis of sterically hindered peptides employing Fmoc-amino acid chlorides in both solution-phase and solid phase methods
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Chenna Krishna
, p. 2625 - 2637 (2008/12/22)
The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF-CH2Cl2 has also been outlined. The final peptide was obtained in 80% yield and was fully characterized. Copyright Taylor & Francis Group, LLC.
Synthesis of Fmoc-protected β-amino alcohols and peptidyl alcohols from Fmoc-amino acid/peptide acid azides
Babu, Vommina V. Suresh,Kantharaju,Sudarshan, Naremaddepalli S.
, p. 1880 - 1886 (2007/10/03)
An efficient synthesis of Nα-9H-fluoren-9- ylmethoxycarbony(Fmoc)-β-amino alcohols by the reduction of Fmoc-α-amino acyl azides employing aqueous NaBH4 as a reducing agent has been described. The reduction is found to be simple and almost complete. All the Fmoc-β-amino alcohols prepared are fully characterized by 1H and 13C NMR and mass spectrometry. Further, the method is extended for the reduction of seven Fmoc-dipeptidyl acids to the corresponding alcohols. Their reduction is also found to be smooth and complete.
