80035-31-0Relevant academic research and scientific papers
Design, synthesis, and antifouling activity of glucosamine-based isocyanides
Umezawa, Taiki,Hasegawa, Yuki,Novita, Ira S.,Suzuki, Junya,Morozumi, Tatsuya,Nogata, Yasuyuki,Yoshimura, Erina,Matsuda, Fuyuhiko
, (2017/07/24)
Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use of such compounds was later banned by the International Maritime Organization (IMO) due to their high toxicity toward marine organisms, resulting in masculinization and imposex. Since the ban, there have been extensive efforts to develop environmentally benign antifoulants. Natural antifouling products obtained from marine creatures have been the subject of considerable attention due to their potent antifouling activity and low toxicity. These antifouling compounds often contain isocyano groups, which are well known to have natural antifouling properties. On the basis of our previous total synthesis of natural isocyanoterpenoids, we envisaged the installation of an isocyano functional group onto glucosamine to produce an environmentally friendly antifouling material. This paper describes an effective synthetic method for various glucosamine-based isocyanides and evaluation of their antifouling activity and toxicity against cypris larvae of the barnacle Amphibalanus amphitrite. Glucosamine isocyanides with an ether functionality at the anomeric position exhibited potent antifouling activity, with EC50 values below 1 μg/mL, without detectable toxicity even at a high concentration of 10 μg/mL. Two isocyanides had EC50 values of 0.23 and 0.25 μg/mL, comparable to that of CuSO4, which is used as a fouling inhibitor (EC50 = 0.27 μg/mL).
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.
Synthesis of glycosides via indium(III) chloride mediated activation of glycosyl halide in neutral condition
Mukherjee, Debaraj,Kumar Ray, Pradip,Sankar Chowdhury, Uday
, p. 7701 - 7704 (2007/10/03)
Various glycosides and disaccharides were synthesized through coupling of glycosyl bromides with acceptors in presence of indium chloride as a promoter. Glycosidation reactions proceeded with high stereoselectivity.
Chemical synthesis of N-acetylglucosamine derivatives and their use as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC
Kamst, Eric,Zegelaar-Jaarsveld, Korien,Van Der Marel, Gijs A.,Van Boom, Jacques H.,Lugtenberg, Ben J.J.,Spaink, Herman P.
, p. 176 - 189 (2007/10/03)
Rhizobial bacteria synthesize lipo-chitin oligosaccharide signal molecules (Nod factors) that are essential for the formation of symbiotic organs on the roots of host plants, a process known as nodulation. Biosynthesis of the chitin oligosaccharide moiety
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
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
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.
Lipid A analog as stimulant for production of interleukin-1 in human monocytes and tumor cell growth inhibitor
-
, (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.
