132286-77-2Relevant articles and documents
The total chemical synthesis of the monoglycosylated GM2 ganglioside activator using a novel cysteine surrogate
Sato, Kohei,Kitakaze, Keisuke,Nakamura, Takahiro,Naruse, Naoto,Aihara, Keisuke,Shigenaga, Akira,Inokuma, Tsubasa,Tsuji, Daisuke,Itoh, Kohji,Otaka, Akira
, p. 9946 - 9948 (2015)
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.
Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry
Sayers, Jessica,Thompson, Robert E.,Perry, Kristen J.,Malins, Lara R.,Payne, Richard J.
supporting information, p. 4902 - 4905 (2015/10/12)
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
Synthesis and biological evaluation (in Vitro and in Vivo) of cyclic arginine-glycine-aspartate (RGD) peptidomimetic-paclitaxel conjugates targeting integrin αvβ3
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 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.
A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives
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)
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%.
Chlorotrimethylsilane Mediated Formation of ω-Allyl Esters of Aspartic and Glutamic Acids
Belshaw, Peter J.,Mzengeza, Shadreck,Lajoie, Gilles A.
, p. 3157 - 3160 (2007/10/02)
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.
