117177-19-2Relevant articles and documents
Facile synthesis of d-lividosamine
Zhan, Zhi-Lai,Ren, Feng-Xia,Zhao, Yi-Min
, p. 315 - 317 (2010)
A simple, four-step synthesis of d-lividosamine starting from N-acetyl-d-glucosamine via a furanosyl oxazoline intermediate is described.
Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization
Laxminarayan, Sahoo,Singhamahapatra, Anadi,Sahoo, Satyanarayan
, p. 539 - 548 (2018/06/19)
A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives.The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation.The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used.The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions.
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.