80035-32-1Relevant academic research and scientific papers
Synthesis of N -acetyl glucosamine analogs as inhibitors for hyaluronan biosynthesis
Wasonga, Gilbert,Tatara, Yota,Kakizaki, Ikuko,Huang, Xuefei
, p. 392 - 409 (2013/10/08)
Elevated hyaluronan expression is a hallmark of many types of cancer. Therefore, inhibition of hyaluronan biosynthesis can potentially slow the growth of tumor cells. Herein, we explore a chain termination strategy to reduce hyaluronan synthesis by tumor cells. Several analogs of glucosamine were prepared, which contained modifications at the C-3 positions. These analogs can possibly cap the nonreducing end of a growing hyaluronan chain, thus lowering the amount of hyaluronan synthesized. Upon incubation with pancreatic cancer cells, a fluorine-containing glucosamine analog was found to exhibit significant inhibitory activities of hyaluronan synthesis. Furthermore, it drastically reduced the proliferation of cancer cells. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.
TCP- and phthalimide-protected n-pentenyl glucosaminide precursors for the synthesis of nodulation factors as illustrated by the total synthesis of nodRf-III (C18:1, MeFuc)
Debenham, John S.,Rodebaugh, Robert,Fraser-Reid, Bert
, p. 4591 - 4600 (2007/10/03)
TCP- and phthalimide-protected n-pentenyl glucosaminide (NPG) precursors have been utilized in a convergent stereocontrolled synthesis of the nodulation factor NodRf-III (C18:1, MeFuc) produced by Rhizobium fredii USDA257, 2. Nodulation factors are lipool
RECTIVITE COMPAREE DE DIVERS ACCEPTEURS DE LA D-GLUCOSAMINE LORS DE LA SYNTHESE DE PRECURSEURS DU CHITOBIOSE
Lafont, Dominique,Boullanger, Paul,Fenet, Bernard
, p. 565 - 584 (2007/10/02)
Six D-glucosamine derivatives, diversely substituted at the nitrogen atom, were tested as acceptors in glycosylation reactions with 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose (1) as the donor and trimethylsilyl trifluoromethanesulfonate as the promoter.The observed yields were high with 2-phthalimido- and 2-azido-D-glucosamine acceptors and more generally good with acceptors of the 1,6-anhydro-D-glucosamine series.The disaccharides benzyl 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (20), benzyl 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (21), 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (22), 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (23), 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (24) and 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (25) have thus been synthesized.
Chemical Synthesis of Nod-Rm-1: the Nodilation Factor Involved in Rhizobium meliloti-legume Symbiosis
Wang, Lai-Xi,Li, Chuan,Wang, Qin-Wei,Hui, Yong-Zheng
, p. 621 - 628 (2007/10/02)
A total synthesis of the sulfated lipotetrasaccharide (NodRm-1) is described.First, the disaccharide glycosyl donor - O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 3a or
Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
Kondo, Hirosato,Aoki, Shin,Ichikawa, Yoshitaka,Halcomb, Randall L.,Ritzen, Helena,Wong, Chi-Huey
, p. 864 - 877 (2007/10/02)
The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides.Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed.When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH.The glycosyl phosphite can also be activated by TMSOTf directly.The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
Towards the Chemoenzymatic Synthesis of Lipid A
Sugai, Takeshi,Ritzen, Helena,Wong, Chi-Huey
, p. 1051 - 1058 (2007/10/02)
New procedures have been developed for the synthesis of the two important components of lipid A; one is the lipase-catalyzed resolution of 3-hydroxytetradecanoic acid in tetrahydrofuran using vinyl acetate and the other is the synthesis of the disaccharide moiety using glycosylphosphite as the glycosylating reagent.
Lipid A analog as stimulant for production of interleukin-1 in human monocytes and tumor cell growth inhibitor
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, (2008/06/13)
This invention concerns the use of synthetic Lipid A analog P9132 to activate human monocytes, and inhibit growth of tumor cells.
Chemistry of Bacterial Endotoxins. Part 2. A Practical Synthesis of 6-O--β-D-glucopyranosyl>-2-deoxy-2--D-glucose
Charon, Daniel,Mondange, Michelle,Szabo, Ladislas
, p. 2291 - 2296 (2007/10/02)
An improved method for the preparation of the phosphorylated disaccharide named in the title, via benzyl 2-amino-6-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside, is described.
Syntheses of derivatives of lacto-N-biose. I. 4,6-Di-O-acetyl-3-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-α,β-D-glucopyranosyl chloride
Lemieux, R. U.,Abbas, S. Z.,Chung, B. Y.
, p. 58 - 62 (2007/10/02)
Procedures are reported for the synthesis of 4,6-di-O-acetyl-3-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-α,β-D-glucopyranosyl chloride, a reagent useful for the reliable introduction of β-D-Galp-(1->3)-β-D-GlcNAcp units (lacto-N-biose
