Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 22, Issue 7, Pages 2090-2101Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2014.02.023
Keywords
Seleno-carbohydrate; Carbohydrate-protein complex; X-ray crystallography; SAD/MAD phasing; Lectin
Funding
- World Premier International Research Center Initiative (WPI), MEXT, Japan
- MEXT of Japan [22380067, 23688014, 24110505]
- Grants-in-Aid for Scientific Research [22380067, 24110505, 23688014] Funding Source: KAKEN
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Seleno-lactoses have been successfully synthesized as candidates for mimicking carbohydrate ligands for human galectin-9 N-terminal carbohydrate recognition domain (NCRD). Selenium was introduced into the mono-or di-saccharides using p-methylselenobenzoic anhydride (Tol(2)Se) as a novel selenating reagent. The TolSe-substituted monosaccharides were converted into selenoglycosyl donors or acceptors, which were reacted with coupling partners to afford seleno-lactoses. The seleno-lactoses were converted to the target compounds. The structure of human galectin-9 NCRD co-crystallized with 6-MeSe-lactose was determined with single/multi-wavelength anomalous dispersion (SAD/MAD) phasing and was similar to that of the co-crystal with natural lactose. (C) 2014 Elsevier Ltd. All rights reserved.
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