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Glycosyltransferase

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https://www.readbyqxmd.com/read/28910600/an-acceptor-analogue-of-%C3%AE-1-4-galactosyltransferase-substrate-inhibitor-or-both
#1
Jingqian Jiang, Gerd K Wagner
Many glycosyltransferase inhibitors in the literature are structurally derived from the donor or acceptor substrate of the respective enzyme. A representative example is 2-naphthyl β-d-GlcNAc, a synthetic GlcNAc glycoside that has been reported as a galactosyltransferase inhibitor. This GlcNAc derivative is attractive as a chemical tool compound for biological and biochemical studies because of its reported potency as an inhibitor, and its short and straightforward synthesis from readily available starting materials...
August 31, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28905966/computational-insights-into-active-site-shaping-for-substrate-specificity-and-reaction-regioselectivity-in-the-extl2-retaining-glycosyltransferase
#2
Fernanda Mendoza, José M Lluch, Laura Masgrau
Glycosyltransferases are enzymes that catalyze a monosaccharide transfer reaction from a donor to an acceptor substrate with the synthesis of a new glycosidic bond. They are highly substrate specific and regioselective, even though the acceptor substrate often presents multiple reactive groups. Currently, many efforts are dedicated to the development of biocatalysts for glycan synthesis and, therefore, a better understanding of how natural enzymes achieve this goal can be of valuable help. To gain a deeper insight into the catalytic strategies used by retaining glycosyltransferases, the wild type EXTL2 (CAZy family GT64) and four mutant forms (at positions 293 and 246) were studied using QM(DFT)/MM calculations and molecular dynamics simulations...
September 14, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28902451/ectopic-expression-of-glycosyltransferase-ugt76e11-increases-flavonoid-accumulation-and-enhances-abiotic-stress-tolerance-in-arabidopsis
#3
Qin Li, Hui-Min Yu, Xia-Fei Meng, Ji-Shan Lin, Yan-Jie Li, Bing-Kai Hou
Although plant glycosyltransferases are thought to play important roles in growth and interaction with environments, little is known about their physiological roles for the most members of plant glycosyltransferase family. We cloned and characterized an Arabidopsis glycosyltransferase gene UGT76E11. Its in vivo physiological effects in flavonoid accumulation and plant tolerance to abiotic stresses were investigated. UGT76E11 gene was up-regulated in transcription expression under various stress conditions including salinity, drought and H2 O2 treatment...
September 13, 2017: Plant Biology
https://www.readbyqxmd.com/read/28901357/an-ortho-c-methylation-o-glycosylation-motif-on-a-hydroxy-coumarin-scaffold-selectively-installed-by-biocatalysis
#4
Alexander Gutmann, Margaretha Schiller, Mandana Gruber-Khadjawi, Bernd Nidetzky
Various bioactive natural products, like the aminocoumarin antibiotics novobiocin and coumermycin, exhibit an aromatic C-methyl group adjacent to a glycosylated phenolic hydroxyl group. Therefore, tailoring of basic phenolic scaffolds to contain the intricate C-methyl/O-glycosyl motif is of high interest for structural and functional diversification of natural products. We demonstrate site-selective 8-C-methylation and 7-O-β-d-glucosylation of 4,5,7-trihydroxy-3-phenyl-coumarin (1) by S-adenosyl-l-methionine dependent C-methyltransferase (from Streptomyces niveus) and uridine 5'-diphosphate glucose dependent glycosyltransferase from apple (Malus × domestica)...
September 13, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28900021/another-brick-in-the-wall-a-rhamnan-polysaccharide-trapped-inside-peptidoglycan-of-lactococcus-lactis
#5
Irina Sadovskaya, Evgeny Vinogradov, Pascal Courtin, Julija Armalyte, Mickael Meyrand, Efstathios Giaouris, Simon Palussière, Sylviane Furlan, Christine Péchoux, Stuart Ainsworth, Jennifer Mahony, Douwe van Sinderen, Saulius Kulakauskas, Yann Guérardel, Marie-Pierre Chapot-Chartier
Polysaccharides are ubiquitous components of the Gram-positive bacterial cell wall. In Lactococcus lactis, a polysaccharide pellicle (PSP) forms a layer at the cell surface. The PSP structure varies among lactococcal strains; in L. lactis MG1363, the PSP is composed of repeating hexasaccharide phosphate units. Here, we report the presence of an additional neutral polysaccharide in L. lactis MG1363 that is a rhamnan composed of α-l-Rha trisaccharide repeating units. This rhamnan is still present in mutants devoid of the PSP, indicating that its synthesis can occur independently of PSP synthesis...
September 12, 2017: MBio
https://www.readbyqxmd.com/read/28892347/two-cooperative-glycosyltransferases-are-responsible-for-the-sugar-diversity-of-saquayamycins-isolated-from-streptomyces-sp-ky-40-1
#6
Shaimaa M Salem, Stevi Weidenbach, Jürgen Rohr
Glycosyltransferases are key enzymes involved in the biosynthesis of valuable natural products providing an excellent drug-tailoring tool. Herein, we report the identification of two cooperative glycosyltransferases from the sqn gene cluster directing the biosynthesis of saquayamycins in Streptomyces sp. KY40-1: SqnG1 and SqnG2. Gene inactivation of sqnG1 leads to 50-fold decrease in saquayamycin production, while inactivation of sqnG2 leads to complete production loss, suggesting that SqnG2 acts as dual O- and C-glycosyltransferase...
September 13, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28889482/tlr-induced-smpd3-defects-enhance-inflammatory-response-of-b-cell-and-macrophage-in-the-pathogenesis-of-sle
#7
Fei Liu, Xiaojing Li, Huimin Yue, Jianjian Ji, Ming You, Liang Ding, Hongye Fan, Yayi Hou
B lymphocyte and macrophages may contribute to SLE pathogenesis through cytokine production after TLR stimulation. Emerging evidences suggested that defects of sphingolipid metabolism was responsible for SLE pathogenesis. However, it is not clear whether these defects exist in B cells and macrophages under SLE condition and whether TLR signaling pathway was related to the dysfunction of sphingolipid metabolism in SLE. Here we demonstrated that the enzymes involved in the sphingolipid metabolism expressed abnormally in B cells from SLE patients and lupus-prone mice...
September 10, 2017: Scandinavian Journal of Immunology
https://www.readbyqxmd.com/read/28881098/identification-and-engineering-of-post-pks-modification-bottlenecks-for-ansamitocin-p-3-titer-improvement-in-actinosynnema-pretiosum-subsp-pretiosum-atcc-31280
#8
Xinjuan Ning, Xinran Wang, Yuanting Wu, Qianjin Kang, Linquan Bai
The type-I polyketide Ansamitocin P-3 (AP-3) is a potent antitumor agent. Its production is most likely hampered by the required multiple substrate supplies and complicated post-PKS modifications in Actinosynnema pretiosum subsp. pretiosum ATCC 31280. For titer improvement, gene ansa30, encoding for a glycosyltransferase competing for the N-demethyl-AP-3 (PND-3) intermediate for AP-3 biosynthesis, was initially inactivated. In the mutant NXJ-22, the AP-3 titer was increased by 66% along with an obvious accumulation of PND-3, indicating that the N-methylation is a rate-limiting step...
September 7, 2017: Biotechnology Journal
https://www.readbyqxmd.com/read/28878590/enzymatically-modified-isoquercitrin-supplementation-intensifies-plantaris-muscle-fiber-hypertrophy-in-functionally-overloaded-mice
#9
Akiko Kohara, Masanao Machida, Yuko Setoguchi, Ryouichi Ito, Masanori Sugitani, Hiroko Maruki-Uchida, Hiroyuki Inagaki, Tatsuhiko Ito, Naomi Omi, Tohru Takemasa
BACKGROUND: Enzymatically modified isoquercitrin (EMIQ) is produced from rutin using enzymatic hydrolysis followed by treatment with glycosyltransferase in the presence of dextrin to add glucose residues. EMIQ is absorbed in the same way as quercetin, a powerful antioxidant reported to prevent disused muscle atrophy by targeting mitochondria and to have ergogenic effects. The present study investigated the effect of EMIQ on skeletal muscle hypertrophy induced by functional overload. METHODS: In Study 1, 6-week-old ICR male mice were divided into 4 groups: sham-operated control, sham-operated EMIQ, overload-operated control, and overload-operated EMIQ groups...
2017: Journal of the International Society of Sports Nutrition
https://www.readbyqxmd.com/read/28860654/heterologous-expression-of-the-n-acetylglucosaminyltransferase-i-dictates-a-reinvestigation-of-the-n-glycosylation-pathway-in-chlamydomonas-reinhardtii
#10
Gaëtan Vanier, Pierre-Louis Lucas, Corinne Loutelier-Bourhis, Jessica Vanier, Carole Plasson, Marie-Laure Walet-Balieu, Philippe Chan Tchi-Song, Isabelle Remy-Jouet, Vincent Richard, Sophie Bernard, Azeddine Driouich, Carlos Afonso, Patrice Lerouge, Elodie Mathieu-Rivet, Muriel Bardor
Eukaryotic N-glycosylation pathways are dependent of N-acetylglucosaminyltransferase I (GnTI), a key glycosyltransferase opening the door to the formation of complex-type N-glycans by transferring a N-acetylglucosamine residue onto the Man5GlcNAc2 intermediate. In contrast, glycans N-linked to Chlamydomonas reinhardtii proteins arise from a GnTI-independent Golgi processing of oligomannosides giving rise to Man5GlcNAc2 substituted eventually with one or two xylose(s). Here, complementation of C. reinhardtii with heterologous GnTI was investigated by expression of GnTI cDNAs originated from Arabidopsis and the diatom Phaeodactylum tricornutum...
August 31, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28860194/the-bacterial-arginine-glycosyltransferase-effector-nleb-preferentially-modifies-fas-associated-death-domain-protein-fadd
#11
Nichollas E Scott, Cristina Giogha, Georgina L Pollock, Catherine L Kennedy, Andrew I Webb, Nicholas A Williamson, Jaclyn S Pearson, Elizabeth L Hartland
The inhibition of host innate immunity pathways is essential for the persistence of attaching and effacing (A/E) pathogens such as enteropathogenic Escherichia coli (EPEC) and Citrobacter rodentium during mammalian infections. To subvert these pathways and suppress the antimicrobial response, A/E pathogens use type III secretion systems (T3SS) to introduce effectors targeting key signaling pathways in host cells. One such effector is the arginine glycosyltransferase NleB1 (NleBCR in C. rodentium) that modifies conserved arginine residues in death domain-containing host proteins with N-acetylglucosamine (GlcNAc), thereby blocking extrinsic apoptosis signaling...
August 31, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28857455/pyruvate-kinase-coupled-glycosyltransferase-assays-limitations-struggles-and-problems-resolutions
#12
Stephane Vincent, Huixiao Fu, Weidong Pan
Enzyme assays involving a coupled pyruvate kinase (PK) have been used for many years to monitor the activity of major classes of enzymes including glycosyltransferases. Numerous potent inhibitors have been discovered and kinetically characterized thanks to this technology. However, when inhibitors of these important enzymes are screened, PK inhibitors or activators are very often observed. In this study, we report solutions to resolve the problems encountered during either the screening or the kinetic characterization of glycosyltransferase inhibitors using a PK coupled assay...
August 30, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28854654/expression-differences-of-resistance-related-genes-induced-by-cycloxaprid-using-qrt-pcr-in-the-female-adult-of-sogatella-furcifera-hemiptera-delphacidae
#13
Jian-Xue Jin, Dao-Chao Jin, Feng-Liang Li, Ying Cheng, Wen-Hong Li, Zhao-Chun Ye, Yu-Hang Zhou
As a newer cis-nitromethylene neonicotinoid pesticide at present, cycloxaprid has good industrialization prospects, including the management of imidacloprid-resistant populations, because this chemical have an excellent efficiency against rice planthoppers. Sogatella furcifera (Horváth) is the most economically important pest of rice worldwide and has developed resistance to many insecticides. This study focused on the expression change of these resistance genes, induced by cycloxaprid, involved in metabolic detoxification and receptor protein...
August 1, 2017: Journal of Economic Entomology
https://www.readbyqxmd.com/read/28853018/improvement-of-the-pharmacological-activity-of-menthol-via-enzymatic-%C3%AE-anomer-selective-glycosylation
#14
Ha-Young Choi, Bo-Min Kim, Abubaker M A Morgan, Joong Su Kim, Won-Gon Kim
Menthol has a considerable cooling effect, but the use range of menthol is limited because of its extremely low solubility in water and inherent flavor. (-)-Menthol β-glucoside was determined to be more soluble in water (>27 times) than (-)-menthol α-glucoside; hence, β-anomer-selective glucosylation of menthol is necessary. The in vitro glycosylation of (-)-menthol by uridine diphosphate glycosyltransferase (BLC) from Bacillus licheniformis generated (-)-menthol β-glucoside and new (-)-menthol β-galactoside and (-)-menthol N-acetylglucosamine...
August 29, 2017: AMB Express
https://www.readbyqxmd.com/read/28844388/cation-exchange-assisted-binding-elution-strategy-for-enzymatic-synthesis-of-human-milk-oligosaccharides-hmos
#15
Hailiang Zhu, Zhigang Wu, Madhusudhan Reddy Gadi, Shuaishuai Wang, Yuxi Guo, Garrett Edmunds, Wanyi Guan, Junqiang Fang
A cation exchange assisted binding-elution (BE) strategy for enzymatic synthesis of human milk oligosaccharides (HMOs) was developed. An amino linker was used to provide the cation ion under acidic condition which can be readily bound to cation exchange resin and then eluted off by saturated ammonium bicarbonate. Ammonium bicarbonate in the collections was easily removed by vacuum evaporation. This strategy circumvented the incompatible issue between glycosyltransferases and solid support or large polymers, and no purification was needed for intermediate products...
September 15, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28842505/the-glycosyltransferase-gnt-iii-activates-notch-signaling-and-drives-stem-cell-expansion-to-promote-the-growth-and-invasion-of-ovarian-cancer
#16
Heba Allam, Blake P Johnson, Mao Zhang, Zhongpeng Lu, Martin J Cannon, Karen L Abbott
Glycosylation changes associated with cellular transformation can facilitate the growth and progression of tumors. Previously we discovered that the gene Mgat3 encoding the glycosyltransferase GnT-III is elevated in epithelial ovarian carcinomas (EOC) and leads to the production of abnormal truncated N-linked glycan structures. In this study we are interested in discovering how these abnormal glycans impact the growth and progression of ovarian cancer. We have discovered using stable shRNA gene suppression that GnT-III expression controls the expansion of side-population cells or cancer stem cells...
August 23, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28842487/loss-of-mucin-type-o-glycans-impairs-the-integrity-of-the-glomerular-filtration-barrier-in-the-mouse-kidney
#17
Kai Song, Jianxin Fu, Jianhua Song, Brett H Herzog, Kirk Bergstrom, Yuji Kondo, J Michael McDaniel, Samuel McGee, Robert Silasi-Mansat, Florea Lupu, Hong Chen, Harini Bagavant, Lijun Xia
The kidney filtration activity is essential for removing toxins and waste products from the body. The vascular endothelial cells of the glomerulus are fenestrated, flattened and are surrounded by podocytes, specialized cells that support the glomerular endothelial cells. Mucin-type core 1-derived O-glycans are highly expressed on both glomerular capillary endothelial cells and their supporting podocytes, but their biological role is unclear. Biosynthesis of core 1-derived O-glycans is catalyzed by the glycosyltransferase C1galt1...
August 25, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28839219/evolutionary-divergence-of-the-abo-and-gbgt1-genes-specifying-the-abo-and-fors-blood-group-systems-through-chromosomal-rearrangements
#18
Fumiichiro Yamamoto
Human alleles at the ABO and GBGT1 genetic loci specify glycosylation polymorphism of ABO and FORS blood group systems, respectively, and their allelic basis has been elucidated. These genes are also present in other species, but presence/absence, as well as functionality/non-functionality are species-dependent. Molecular mechanisms and forces that created this species divergence were unknown. Utilizing genomic information available from GenBank and Ensembl databases, gene order maps were constructed of a chromosomal region surrounding the ABO and GBGT1 genes from a variety of vertebrate species...
August 24, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28832049/an-enzymatic-strategy-to-asymmetrically-branched-n-glycans
#19
Angie D Calderon, Jun Zhou, Wanyi Guan, Zhigang Wu, Yuxi Guo, Jing Bai, Qing Li, Peng George Wang, Junqiang Fang, Lei Li
An enzymatic strategy was developed to generate asymmetrically branched N-glycans from natural sources by using a panel of glycosidases and glycosyltransferases. Briefly, LacZ β-galactosidase was employed to selectively trim symmetrically branched N-glycans isolated from bovine fetuin. The yielding structures were then converted to asymmetrically branched core structures by robust glycosyltransferase for further extension.
September 13, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28830101/transparent-testa-16-and-15-act-through-different-mechanisms-to-control-proanthocyanidin-accumulation-in-arabidopsis-testa
#20
W Xu, S Bobet, J Le Gourrierec, D Grain, D De Vos, A Berger, F Salsac, Z Kelemen, J Boucherez, A Rolland, G Mouille, J M Routaboul, L Lepiniec, C Dubos
Flavonoids are secondary metabolites that fulfil a multitude of functions during the plant life cycle. In Arabidopsis proanthocyanidins (PAs) are flavonoids that specifically accumulate in the innermost integuments of the seed testa (i.e. endothelium), as well as in the chalaza and micropyle areas, and play a vital role in protecting the embryo against various biotic and abiotic stresses. PAs accumulation in the endothelium requires the activity of the MADS box transcription factor TRANSPARENT TESTA (TT) 16 (ARABIDOPSIS B-SISTER/AGAMOUS-LIKE 32) and the UDP-glycosyltransferase TT15 (UGT80B1)...
May 17, 2017: Journal of Experimental Botany
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