54829-37-7Relevant academic research and scientific papers
Small ring constrained peptidomimetics. Synthesis of epoxy peptidomimetics, inhibitors of cysteine proteases
Demarcus,Ganadu,Mura,Porcheddu,Quaranta,Reginato,Taddei
, p. 697 - 706 (2007/10/03)
Different dipeptide analogues containing an oxirane ring in the place of the peptidic bond were prepared starting from naturally occurring amino acids. N-Fmoc-amino aldehydes were transformed into the corresponding methoxyvinyl derivatives through a Wittig reaction, and the addition of PhSeCl gave a series of different α-phenylselenyl aldehydes. Mukajiama reaction with silylketene acetals gave an intermediate product that was finally transformed into the desired oxiranyl peptidomimetics. Following this strategy we were able to control three new contiguous stereocenters starting from the enantiomerically pure amino acid. The dipeptide analogues could be used in SPPS on a SASRIN resin as the final epoxides were relatively unstable under acidic conditions. Moreover the synthesis of the single dipeptide mimetics was carried out on solid phase to generate a small library of epoxy peptidomimetics. Some of the products prepared in this work resulted as time-dependent reversible inhibitors of cysteine protease.
A CONVENIENT ONE-POT PROCEDURE FOR SYNTHESIS OF THIOL ESTERS USING MAGNESIUM ION AS A CATALYST
Ohta, Shunsaku,Okamoto, Masao
, p. 3245 - 3246 (2007/10/02)
Various thiol esters (R1COSR2) were prepared in high yields by treatment of 1-acylimidazole with thiols in the presence of a catalytic amount of Mg(OEt)2.Malonic half-thiol esters 1OCOCH(R3)COSR2> were also prepared in good yields by treating magnesium monoalkyl malonate 1OCOCH(R3)COOMg0.5> with carbonyl-1,1'-diimidazole followed by addition of thiols.
