Glycosylamine

Under conditions, the reaction of tetra-o-acetyl-o-glucopyranosyl bromide with A-4-thiazoline-2-thione provides the glycosylamine (76) (N-alkylation) (Scheme 36) (163). However, treatment of 5-... 

Stereoselective Strecker reactions with galactosylamine 1 can also be achieved with sodium cyanide and acetic acid in 2-propanol. The reactions, however, proceed slowly and with a lower stereoselectivity, giving diastereomeric ratios of the products between 3 1 and 7 1. The scope of the method can be extended to other glycosylamines, e.g., 2,3,4-tri-O-pivaloyl-a-D-arabinosyl-amine which allows the stereoselective synthesis of (A )-amino nitriles61,62. 

Monosaccharides in which an alcoholic hydroxy group has been replaced by an amino group are called amino sugars (see 2-Carb-14). When the hemiacetal hydroxy group is replaced, the compounds are called glycosylamines. 

When the amino group is at the anomeric position, the compound is normally named as a glycosylamine (see 2-Carb-33.6). 

N-Glycosyl derivatives are conveniently named as glycosylamines. In the case of complex heterocyclic amines, such as nucleosides, the same approach is used. 

Carba-glycosylamines [2,3,4-trihydroxy-5-(hydroxymethyl)-1 -cyclohex-ylamine] and related compounds are well known to exist as components of the antibiotic validamycin complex and carba-oligosaccharidic alpha amylase inhibitors. ... 

Microbial degradation of validamycin A (8) with a cell suspension of Pseudomonas dentrificans afforded validamine (202) and valienamine (203). Hydrogenolysis of validamycin B, followed by acid hydrolysis, yielded hydroxy validamine (204). Valiolamine (205) was isolated and shown to be a component of validamycin G. ° Biosynthesis of these carba-glycosylamines was extensively studied, and the intramolecular aldol addition of the... 

Inhibitory Activity of Some Carba-glycosylamines against Three Enzymes... 

Results of inhibition studies with nojirimycin and its analogs published up to 1988, and additional data from the author s laboratory, are summarized in Table VI. It should be noted that the inhibition constants are given in pM instead of mM (as in Tables II - V). Data for glycosylamines are included, in order to facilitate an estimation of the effects caused by the different positions of the basic group in the two types of basic sugar derivative. Not included are the data of Reese and coworkers and of Grover and Cushley on nojirimycin, because these authors were apparently unaware of the slow and only partial dissociation of the nojirimycin hydrogensulfite adduct which had been used instead of free nojirimycin. 

Inhibition of a- and Glycosidases by the Respective 5-Amino-5-deoxyhexopyranoses, 1,5-Dideoxy-],5-iminohexitoIs, and Glycosylamines... 

Enzyme and source 5-Amino-S-deoxy- hexopyranose 1,5-Dideoxy- 1,5-iminohexitol Glycosylamine References... 

Ferndndez-Bolanos JG, Lopez 6 (2007) Synthesis of Heterocycles from Glycosylamines and Glycosyl Azides. 7 31-66... 

---