Add time:08/21/2019         Source:sciencedirect.com

Hydrazides of five N-acylamino acids have been used alone as substrates for papain catalysis to yield N1,N2-diacylhydrazines. With the exception of N-(benzyloxycarbonyl)(Z)-d-alanine hydrazide, they were very effective as both acylating agents of the enzyme and nucleophiles in attacking the enzyme-substrate intermediate. Although Z-d-alanine hydrazide was a minimal acylating agent, it was a satisfactory nucleophile. The most favorable reaction involved Z-l-alanine hydrazide in producing N1,N2-bis(Z-l-alanyl)hydrazine. When Z-dl-alanine hydrazide was the substrate, this same chiral diacylhydrazine was formed along with meso N1-(Z-d-alanyl)-N2-(Z-l-alanyl)hydrazine. For the acylation step, the enzyme displayed powerful, essentially stereospecific, bias toward the l enantiomer. Once the thioester intermediate was formed, little preference was detected for attack by the enantiomers as nucleophiles. The most direct procedure for synthesis of substrates was conversion of Z-amino acids to their esters by means of dry HCl in an absolute alcohol. Treatment with hydrazine produced the hydrazides in excellent yield.

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