Expanded potential of seleno-carbohydrates as a molecular tool for X-ray structural determination of a carbohydrate-protein complex with single/multi-wavelength anomalous dispersion phasing

Tatsuya Suzuki; Hisayoshi Makyio; Hiromune Ando; Naoko Komura; Masanori Menjo; Yusuke Yamada; Akihiro Imamura; Hideharu Ishida; Soichi Wakatsuki; Ryuichi Kato; Makoto Kiso

doi:10.1016/j.bmc.2014.02.023

Expanded potential of seleno-carbohydrates as a molecular tool for X-ray structural determination of a carbohydrate-protein complex with single/multi-wavelength anomalous dispersion phasing

Bioorg Med Chem. 2014 Apr 1;22(7):2090-101. doi: 10.1016/j.bmc.2014.02.023. Epub 2014 Feb 25.

Authors

Affiliations

¹ Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan; Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501, Japan.
² Structural Biology Research Center, Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), 1-1 Oho, Tsukuba, Ibaraki 305-0801, Japan.
³ Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan; Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501, Japan. Electronic address: [email protected].
⁴ Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
⁵ Structural Biology Research Center, Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), 1-1 Oho, Tsukuba, Ibaraki 305-0801, Japan; Photon Science, SLAC Natl. Accelerator Laboratory Structure Science, 2575 Sand Hill Road, MS 69, Menlo Park, CA 94025-7015, USA; Department of Structural Biology, Stanford University, Beckman Center B105, 279 Campus Drive, Stanford, CA 94305-5126, USA.

PMID: 24631362
DOI: 10.1016/j.bmc.2014.02.023

Abstract

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 (Tol2Se) 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.

Keywords: Carbohydrate–protein complex; Lectin; SAD/MAD phasing; Seleno-carbohydrate; X-ray crystallography.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrates / chemical synthesis
Carbohydrates / chemistry*
Crystallography, X-Ray
Galectins / chemistry*
Humans
Models, Molecular
Molecular Structure
Organoselenium Compounds / chemical synthesis
Organoselenium Compounds / chemistry*

Substances

Carbohydrates
Galectins
LGALS9 protein, human
Organoselenium Compounds