73448-32-5Relevant academic research and scientific papers
Synthesis of 2-[(2-pyridyl)amino]ethyl β-D-lactosaminide and evaluation of its acceptor ability for sialyltransferase: A comparison with 4-methylumbelliferyl and dansyl β-D-lactosaminide
Kajihara, Yasuhiro,Kamiyama, Daisuke,Yamamoto, Naoki,Sakakibara, Tohru,Izumi, Masayuki,Hashimoto, Hironobu
, p. 1545 - 1550 (2004)
We reported the synthesis of β-D-lactosaminide with a 2-aminopyridyl group that is linked to a glycosyl tether at the reducing end. This fluorescent disaccharide acts as an acceptor for both α-(2→6)- and α-(2→3)-sialyltransferases. In addition, the acceptor ability of this disaccharide was evaluated and compared with that of β-D-lactosaminide having a dansyl or a 4-methylumbelliferyl group.
A High-Throughput Glycosyltransferase Inhibition Assay for Identifying Molecules Targeting Fucosylation in Cancer Cell-Surface Modification
Zhang, Xiaohua,Chen, Fei,Petrella, Alessandro,Chacón-Huete, Franklin,Covone, Jason,Tsai, Teng-Wei,Yu, Ching-Ching,Forgione, Pat,Kwan, David H.
, p. 715 - 724 (2019/03/26)
In cancers, increased fucosylation (attachment of fucose sugar residues) on cell-surface glycans, resulting from the abnormal upregulation of the expression of specific fucosyltransferase enzymes (FUTs), is one of the most important types of glycan modifications associated with malignancy. Fucosylated glycans on cell surfaces are involved in a multitude of cellular interactions and signal regulation in normal biological processes, as well as in disease. For example, sialyl LewisX is a fucosylated cell-surface glycan that is abnormally abundant in some cancers where it has been implicated in facilitating metastasis, allowing circulating tumor cells to bind to the epithelial tissue within blood vessels and invade into secondary sites by taking advantage of glycan-mediated interactions. To identify inhibitors of FUT enzymes as potential cancer therapeutics, we have developed a novel high-throughput assay that makes use of a fluorogenically labeled oligosaccharide as a probe of fucosylation. This probe, which consists of a 4-methylumbelliferyl glycoside, is recognized and hydrolyzed by specific glycoside hydrolase enzymes to release fluorescent 4-methylumbelliferone, yet when the probe is fucosylated prior to treatment with the glycoside hydrolases, hydrolysis does not occur and no fluorescent signal is produced. We have demonstrated that this assay can be used to measure the inhibition of FUT enzymes by small molecules, because blocking fucosylation will allow glycosidase-catalyzed hydrolysis of the labeled oligosaccharide to produce a fluorescent signal. Employing this assay, we have screened a focused library of small molecules for inhibitors of a human FUT enzyme involved in the synthesis of sialyl LewisX and demonstrated that our approach can be used to identify potent FUT inhibitors from compound libraries in microtiter plate format.
Highly efficient chemoenzymatic synthesis of β1-4-linked galactosides with promiscuous bacterial β1-4-galactosyltransferases
Lau, Kam,Thon, Vireak,Yu, Hai,Ding, Li,Chen, Yi,Muthana, Musleh M.,Wong, Denton,Huang, Ronald,Chen, Xi
supporting information; experimental part, p. 6066 - 6068 (2010/10/20)
Two bacterial β1-4-galactosyltransferases, NmLgtB and Hp1-4GalT, exhibit promiscuous and complementary acceptor substrate specificity. They have been used in an efficient one-pot multienzyme system to synthesize LacNAc, lactose, and their derivatives including those containing negatively charged 6-O-sulfated GlcNAc and C2-substituted GlcNAc or Glc, from monosaccharide derivatives and inexpensive Glc-1-P.
SUGAR CHAIN CONTAINING 4-POSITION HALOGENATED GALACTOSE AND APPLICATION THEREOF
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Page/Page column 9-10, (2009/01/24)
The present invention is directed to, for example, an oligosaccharide having at an end thereof a 4-position halogenated galactose residue represented by formula (I): (wherein X represents a halogen atom, and R represents a monosaccharide, an oligosaccharide, or a carrier), a transferase inhibitor containing the oligosaccharide, and a method for inhibiting sugar chain elongation reaction in the presence of glycosyltransferase, the method including employing the inhibitor. The invention also provides a method for producing a 4-position halogenated galactose sugar nucleotide represented by formula (II): (wherein each of R1 to R3 represents a hydroxyl group, an acetyl group, a halogen atom, or a hydrogen atom; X represents a halogen atom; and M represents a hydrogen ion or a metal ion), wherein the method employs bacterium-derived galactokinase and bacterium-derived hexose-1-phosphate uridylyltransferase. The invention is also directed to a sugar chain containing 4-position halogenated galactose envisaged to be employed as drugs and other materials, and to applications of the compound.
