Synthesis of D-Galactopyranosylphosphonic and (D-Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases

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Title:Synthesis of D-Galactopyranosylphosphonic and (D-Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases
Creators:
Heissigerová, Helena
Kočalka, Petr
Hlaváčková, Martina
Imberty, Anne
Breton, Christelle
Chazalet, Valerie
Moravcová, Jitka
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 11-12, pp. 1659-1672
Uncontrolled Keywords:Phosphonates, <i>C</i>-Glycosides, Michaelis-Arbuzov reaction, Galactosyltransferases, UDP-Gal, Carbohydrates

Abstract

Employing the Michaelis-Arbuzov reaction of 1-<i>O</i>-acetyl-2,3,4,6-tetra-<i>O</i>-benzyl-D-galactopyranose with triethyl phosphite and trimethylsilyl trifluoromethanesulfonate, α- and β-D-galactopyranosylphosphonic acids were prepared in 33 and 28% yields, respectively. (α-D-Galactopyranosylmethyl)phosphonic acid was synthesized by a five-step route from 2,3,4,6-tetra-<i>O</i>-benzyl-D-galactopyranose in 52% overall yield. When tested against bovine α-1,3- and β-1,4-galactosyltransferases, all three compounds showed, at best, very poor inhibitions. Both enzymes were inhibited more effectively by β-D-galactopyranosylphosphonic acid (IC<sub>50</sub> = 17 mmol l<sup>-1</sup> at 13.5 μmol l<sup>-1</sup> of UDP-Gal for β4GalT). <p>

Title:Synthesis of D-Galactopyranosylphosphonic and (D-Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases
Creators:
Heissigerová, Helena
Kočalka, Petr
Hlaváčková, Martina
Imberty, Anne
Breton, Christelle
Chazalet, Valerie
Moravcová, Jitka
Uncontrolled Keywords:Phosphonates, <i>C</i>-Glycosides, Michaelis-Arbuzov reaction, Galactosyltransferases, UDP-Gal, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:71
Number:11-12
Page Range:pp. 1659-1672
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061659UNSPECIFIED
ID Code:2568
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Heissigerová, Helena; Kočalka, Petr; Hlaváčková, Martina; Imberty, Anne; Breton, Christelle; Chazalet, Valerie; Moravcová, Jitka (2006) Synthesis of D-Galactopyranosylphosphonic and (D-Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases. Collection of Czechoslovak Chemical Communications, 71 (11-12). pp. 1659-1672. ISSN 0010-0765

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