Synthesis of α-D-glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4- methylumbelliferone, a fluorogenic substrate for endo-α-1,2-mannosidase

Article abstract of DOI:10.1080/07328300008544148

α-D-Glucopyranosyl-(1-3)-α-D-mannopyranosyl-(1-7)-4- methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-α-1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-β-D-mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethane-sulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated α-D-glucopyranosyl-(1-3)-α-D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as a substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the α-glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 μg and with time up to 2 h. V_max and K_m were determined to be 0.17 nmol/mg × h and 3.7 mM, respectively.

Full text of DOI:10.1080/07328300008544148

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Journal of Carbohydrate Chemistry
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Synthesis of α-D-Glucopyranosyl-
(1-3)-α-D-Mannopyranosyl-
(1-7)-4-Methylumbelliferone,
A Fluorogenic Substrate for
Endo-α-1,2-Mannosidase
C. Vogel & G. Pohlentz
a Institut für Physiologische Chemie , Universität Bonn,
Nussallee , 11, D-53115 Bonn, Germany
b Institut für Physiologische Chemie , Universität Bonn,
Nussallee , 11, D-53115 Bonn, Germany
Published online: 27 Feb 2008.
To cite this article: C. Vogel & G. Pohlentz (2000) Synthesis of α-D-Glucopyranosyl-
(1-3)-α-D-Mannopyranosyl-(1-7)-4-Methylumbelliferone, A Fluorogenic Substrate for
Endo-α-1,2-Mannosidase, Journal of Carbohydrate Chemistry, 19:9, 1247-1258, DOI:
10.1080/07328300008544148
To link to this article: http://dx.doi.org/10.1080/07328300008544148
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