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The total chemical synthesis of the monoglycosylated GM2 ganglioside activator using a novel cysteine surrogate
We describe a novel peptide ligation/desulfurization strategy using a β-mercapto-N-glycosylated asparagine derivative. The newly developed procedure was successfully applied to the total chemical synthesis of the GM2 ganglioside activator protein bearing a monosaccharide on the native glycosylation site.
Sato, Kohei,Kitakaze, Keisuke,Nakamura, Takahiro,Naruse, Naoto,Aihara, Keisuke,Shigenaga, Akira,Inokuma, Tsubasa,Tsuji, Daisuke,Itoh, Kohji,Otaka, Akira
p. 9946 - 9948
(2015)
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Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry
The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the
Sayers, Jessica,Thompson, Robert E.,Perry, Kristen J.,Malins, Lara R.,Payne, Richard J.
supporting information
p. 4902 - 4905
(2015/10/12)

Synthesis and biological evaluation (in Vitro and in Vivo) of cyclic arginine-glycine-aspartate (RGD) peptidomimetic-paclitaxel conjugates targeting integrin αvβ3
A small library of integrin ligand-paclitaxel conjugates 10-13 was synthesized with the aim of using the tumor-homing cyclo[DKP-RGD] peptidomimetics for site-directed delivery of the cytotoxic drug. All the paclitaxel-RGD constructs 10-13 inhibited biotinylated vitronectin binding to the purified αVβ3 integrin receptor at low nanomolar concentration and showed in vitro cytotoxic activity against a panel of human tumor cell lines similar to that of paclitaxel. Among the cell lines, the cisplatin-resistant IGROV-1/Pt1 cells expressed high levels of integrin αVβ3, making them attractive to be tested in in vivo models. cyclo[DKP-f3-RGD]-PTX 11 displayed sufficient stability in physiological solution and in both human and murine plasma to be a good candidate for in vivo testing. In tumor-targeting experiments against the IGROV-1/Pt1 human ovarian carcinoma xenotransplanted in nude mice, compound 11 exhibited a superior activity compared with paclitaxel, despite the lower (about half) molar dosage used.
Colombo, Raffaele,Mingozzi, Michele,Belvisi, Laura,Arosio, Daniela,Piarulli, Umberto,Carenini, Nives,Perego, Paola,Zaffaroni, Nadia,De Cesare, Michelandrea,Castiglioni, Vittoria,Scanziani, Eugenio,Gennari, Cesare
supporting information
p. 10460 - 10474
(2013/02/22)

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)

Chlorotrimethylsilane Mediated Formation of ω-Allyl Esters of Aspartic and Glutamic Acids
The protection of the ω-carboxylic function of aspartic and glutamic acids by an allyl ester is advantageous because of its orthogonality with most protecting groups and its compatibility with a number of reagents.In this communication we describe a simple method using chlorotrimethylsilane in the presence of allyl alcohol which gives exclusively the ω-allyl esters of both aspartic and glutamic acids in excellent yield.
Belshaw, Peter J.,Mzengeza, Shadreck,Lajoie, Gilles A.
p. 3157 - 3160
(2007/10/02)