Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 25, Issue 3, Pages 1132-1142Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2016.12.021
Keywords
Seleno-carbohydrate; Carbohydrate-protein complex; X-ray crystallography; SAD/MAD phasing; Lectin
Funding
- World Premier International Research Center Initiative (WPI), Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan
- MEXT, Japan [15H04495, 26110704]
- Grants-in-Aid for Scientific Research [15H04495, 26110704] Funding Source: KAKEN
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Selenium-incorporated fucoses (seleno-fucoses) differing in the position of the seleno-substituent were synthesized and applied to the X-ray structural determination of a carbohydrate-lectin complex using single/multi-wavelength anomalous dispersion (SAD/MAD) phasing. The hydroxyl groups at the C-1, -2, -3 and -4 position of fucose were individually substituted with a methylseleno group via a transacetalization reaction using MeSeCH2OBn or by an S(N)2 reaction with TolSe-equivalents to afford the corresponding MeSe-fucose. The three-dimensional structures of a fucose-binding lectin complexed with several of these MeSe-fucoses have been determined by SAD/MAD phasing by utilizing the diffraction of selenium in the bound MeSe-fucoses. (C) 2016 Elsevier Ltd. All rights reserved.
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