113833-08-2Relevant academic research and scientific papers
Glycosidation, X. Synthesis of Glycoconjugates of Acetal-glycosides with Lysine and Tripeptides for Selective Cancer Therapy
Tietze, Lutz F.,Goerlach, Ada,Beller, Matthias
, p. 565 - 578 (2007/10/02)
Acetal-glycosides 6 of cytotoxic aldehydes are a new class of compounds which may be of interest for cancer therapy, because of the possibility of a selective release of the cytotoxic principle in the tumour.For a selective transport to the tumour, these compounds will be connected to monoclonal antibodies, which bond specifically to tumour-associated surface antigens. - In this paper the synthesis of acetal-glycosides 14a-d and 15a-d with a COOH-functionalised spacer and their connection to a lysine derivative 13 and a tripeptide 25 is described.The synthesis of 14a-d and 15a-d was performed by reaction of the acetals 7a-d and 8a-d wit h trimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1) in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate to 9a-d and 10a-d followed by solvolysis and hydrolysis.The connection of 14a-d and 15a-d with 13 and of 14b,d with 25 to the glycoconjugates 20a-d, 21a-d, and 26a-b, respectively, was carried out with hydroxybenzotriazol via the activated esters 18 and 19.
