2008年1月
Target-specific chemical acylation of lectins by ligand-tethered DMAP catalysts
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- 巻
- 130
- 号
- 1
- 開始ページ
- 245
- 終了ページ
- 251
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/ja075684q
- 出版者・発行元
- AMER CHEMICAL SOC
Because sugar-binding proteins, so-called lectins, play important roles in many biological phenomena, the lectin-selective labeling should be useful for investigating biological processes involving lectins as well as providing molecular tools for analysis of saccharides and these derivatives. We describe herein a new strategy for lectin-selective labeling based on an acyl transfer reaction directed by ligand-tethered DIVIAP (4-dimethylaminopyridine). DIVIAP is an effective acyl transfer catalyst, which can activate an acyl ester for its transfer to a nucleophilic residue. To direct the acyl transfer reaction to a lectin of interest, we attached the DIVIAP to a saccharide ligand specific for the target lectin. It was clearly demonstrated by biochemical analyses that the target-selective labeling of Congerin II, an animal lectin having selective affinity for Lactose/LacNAc (N-acetyllactosamine), was achieved in the presence of Lac-tethered DMAPs and acyl donors containing probes such as fluorescent molecules or biotin. Conventional peptide mapping experiments using HPLC and tandem mass-mass analysis revealed that the acyl transfer reaction site-specifically occurred at Tyr 51 of Cong II. This strategy was successfully extended to other lectins by changing the ligand part of the ligand-tethered DMAP. We also demonstrated that this labeling method is applicable not only to purified lectin in test tubes, but also to crude mixtures such as E coli lysates or homogenized animal tissue samples expressing Congerin.
- リンク情報
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- DOI
- https://doi.org/10.1021/ja075684q
- J-GLOBAL
- https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200902296699091187
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/18076168
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000252127500045&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/ja075684q
- ISSN : 0002-7863
- eISSN : 1520-5126
- J-Global ID : 200902296699091187
- PubMed ID : 18076168
- Web of Science ID : WOS:000252127500045