title: Hexosamine analogs: from metabolic glycoengineering to drug discovery.
abstract: Metabolic glycoengineering, a technique pioneered almost two decades ago wherein monosaccharide analogs are utilized to install non-natural sugars into the glycocalyx of mammalian cells, has undergone a recent flurry of advances spurred by efforts to make the methodology more efficient. This article describes the versatility of metabolic glycoengineering, which is a prime example of 'chemical glycobiology,' and gives an overview of its capability to endow complex carbohydrates in living cells and animals with interesting (and useful!) functionalities. Then an overview is provided describing how acylated monosaccharides, a class of molecules originally intended to be efficiently-used, membrane-permeable metabolic intermediates, have led to the discovery that a subset of these compounds (e.g. tributanoylated hexosamines) display unanticipated 'scaffold-dependent' activities; this finding establishes these molecules as a versatile platform for drug discovery.
authors.affiliation: Department of Biomedical Engineering, The Johns Hopkins University, Baltimore, MD 21218, USA.
authors.forename: Zhiyun
authors.initials: Z
authors.lastname: Wang
authors.forename: Jian
authors.initials: J
authors.lastname: Du
authors.forename: Pao-Lin
authors.initials: PL
authors.lastname: Che
authors.forename: M Adam
authors.initials: MA
authors.lastname: Meledeo
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Yarema
mesh_terms: D000818:Animals; D057005:Bioengineering / Q000379:methods*; D001688:Biological Products / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D001704:Biopolymers / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D055808:Drug Discovery / Q000379:methods*; D006595:Hexosamines / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism*; D006801:Humans
chemical_list: D001688:Biological Products; D001704:Biopolymers; D006595:Hexosamines