117194-52-2Relevant academic research and scientific papers
THE SYNTHESIS OF A Nγ-PHTHALYL-Nα-METHYL-α,γ-DIAMINOBUTYRYL CONGENER OF VIRGINIAMYCIN S1
Anteunis, M. J. O.,Auwera, C. Van der,Vanfleteren, L.,Borremans, F.
, p. 135 - 148 (2007/10/02)
A synthesis of (A2bu=α,γ-diaminobutyric acid) is reported using the very efficient coupling agent BOP-Cl (N,N'-bis(3-oxo-2-oxazolidinyl)phosphinic chloride) for imino acid peptide bond formation.The total yield is 11percent for the 5 coupling steps and one lactonization.The final step was a cyclization between residues 5 and 6, after (I) first t-Boc acidic deprotection with 85percent HCOOH of the linear precursor Z-Thr(Nα-Boc-Phg-O-)-D-Abu-Pro-MePhe-MeA2bu(γPht)-OBut followed by (ii) acidic saponification (Tfa) of the t-Bu ester.This sequence was found to be prerequisite, in view of the extreme lability of the 4-5 peptide bond under acidic conditions.
