56047-47-3Relevant academic research and scientific papers
Single-step enzymatic conversion of peptide amides to esters
Meos, Helle,Haga, Mati,Tougu, Vello
, p. 2343 - 2346 (1995)
It is shown that the C-terminal amide groups in N-protected peptides could be efficiently replaced by ester groups via kinetically-controlled papain-catalyzed acyl transfer reactions in aqueous methanol. The specificity of papain was substantially shifted towards the cleavage of C-terminal amide bond in dipeptide substrates by methanol, thus suppressing undesired peptide bond cleavage during esterification.
Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification
Huy, Peter H.,Mbouhom, Christelle
, p. 7399 - 7406 (2019/08/20)
A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.
N-TERMINAL SUBSTITUENT AND SIDE-CHAIN INFLUENCES ON THE CHEMICAL SHIFTS OF PROTONS IN MODEL DIPEPTIDE SYSTEMS
Davies, John S.,Hakeem, Essam
, p. 1387 - 1392 (2007/10/02)
(1)H Chemical shift values of ester methyls in model dipeptide esters have been shown to be sensitive to (a) the nature and configuration of the constituent amino acids and (b) the spatial distance between the N-terminal aryl group and the ester protons.C
Studies on the Diastereoisomeric and Conformational Aspects of Benzoyl Dipeptide Esters, as a Means of assessing Racemisation using Nuclear Magnetic Resonance Spectroscopy
Davies, John S.,Thomas, R. John
, p. 1639 - 1646 (2007/10/02)
Distinct methyl ester signals in the 1H n.m.r. spectra of diastereoisomeric forms of benzoyl dipeptide methyl esters provide a means of estimating the isomer composition of diastereoisomeric mixtures.Analysis of the mixture derived from peptide-coupling r
