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Title: Synthesis and evaluation of a radioiodinated trisaccharide derivative as a synthetic substrate for a sensitive N-acetylglucosaminyltransferase V radioassay.
Authors: Mukai, Takahiro
Hagimori, Masayori
Arimitsu, Kenji
Katoh, Takahiro
Ukon, Misa
Kajimoto, Tetsuya
Kimura, Hiroyuki  KAKEN_id
Magata, Yasuhiro
Miyoshi, Eiji
Taniguchi, Naoyuki
Node, Manabu
Saji, Hideo  kyouindb  KAKEN_id
Author's alias: 木村, 寛之
佐治, 英郎
Keywords: N-acetylglucosaminyltransferase V
Radiolabeled substrate
Radioassay
Issue Date: 15-Jul-2011
Publisher: Elsevier Ltd.
Journal title: Bioorganic & medicinal chemistry
Volume: 19
Issue: 14
Start page: 4312
End page: 4321
Abstract: N-acetylglucosaminyltransferase V (GnT-V) is one of the most relevant glycosyltransferases to tumor invasion and metastasis. Based on previous findings of molecular recognition between GnT-V and synthetic substrates, we designed and synthesized a p-iodophenyl-derivatized trisaccharide, 2-(4-iodophenyl)ethyl 6-O-[2-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-α-d-mannopyranosyl]-β-d-glucopyranoside (IPGMG, 1) and its radiolabeled form, [(125)I]IPGMG ([(125)I]1), for use in assays of GnT-V activity in vitro. The tributyltin derivative, 2-[4-(n-tributylstannyl)phenyl]ethyl 6-O-[2-O-(3, 4, 6-tri-O-acetyl-2-acetamido-2-deoxy-β-d-glucopyranosyl)-3, 4, 6-tri-O-acetyl-α-d-mannopyranosyl]-2, 3, 4-tri-O-acetyl-β-d-glucopyranoside (21), was synthesized as a precursor for the preparation of [(125)I]1. The iododestannylation of 21 using hydrogen peroxide as an oxidant followed by deacetylation yielded [(125)I]1. When [(125)I]1 was incubated in GnT-V-expressing cells with a UDP-GlcNAc donor, the production of β1-6GlcNAc-bearing IPGMG (IPGGMG, 2) was confirmed by radio-HPLC. In kinetic analysis, 1 was found to be a good substrate with a K(m) of 23.7μM and a V(max) of 159pmol/h. μg protein. [(125)I]1 would therefore be a useful synthetic substrate for the quantitative determination of GnT-V activity.
Rights: © 2011 Elsevier Ltd.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/143686
DOI(Published Version): 10.1016/j.bmc.2011.05.047
PubMed ID: 21696968
Appears in Collections:Journal Articles

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