A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives
Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of β-protected Asp and γ-protected Glu derivatives using Alcalase are described. The first method is based on the α-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) α-selective enzymatic methyl-esterification, (ii) chemical β-esterification, and finally (iii) α-selective enzymatic methyl ester hydrolysis. The yields of the purified β- and γ-esters range from 77% to 91%.
Nuijens, Timo,Kruijtzer, John A.W.,Cusan, Claudia,Rijkers, Dirk T.S.,Liskamp, Rob M.J.,Quaedflieg, Peter J.L.M.
experimental part
p. 2719 - 2721
(2009/09/06)
Synthesis and electrochemical properties of tetrathiafulvalene derived amino acids and peptides
A synthetic route to a tetrathiafulvalene (TTF) derived aspartic acid derivative 18, with suitable orthogonal protecting groups has been developed. The aspartic acid derivative 18 can be used in the synthesis of peptides, as exemplified by the synthesis of di-, tri- and tetra-peptides 21-23. Preliminary electrochemical studies of these novel peptides indicate that they may well undergo conformational reorganisation upon oxidation of the TTF moieties.
Booth, Susan,Wallace, Emma N. K.,Singhal, Kavita,Bartlett, Philip N.,Kilburn, Jeremy D.
p. 1467 - 1474
(2007/10/03)
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