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Synthesis of seleno-fucose compounds and their application to the X-ray structural determination of carbohydrate-lectin complexes using single/multi-wavelength anomalous dispersion phasing.

Abstract：

: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 SN2 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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Shimabukuro J,Makyio H,Suzuki T,Nishikawa Y,Kawasaki M,Imamura A,Ishida H,Ando H,Kato R,Kiso M

doi

10.1016/j.bmc.2016.12.021

subject

Has Abstract

pub_date

2017-02-01 00:00:00

pages

1132-1142

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)31172-5

journal_volume

25

pub_type

杂志文章

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