5- amino-5-deoxy

Another microbial polysaccharide-based emulsifier is Hposan, produced by the yeast Candida lipolytica when grown on hydrocarbons (223). Liposan is apparentiy induced by certain water-immiscible hydrocarbons. It is composed of approximately 83% polysaccharide and 17% protein (224). The polysaccharide portion consists of D-glucose, D-galactose, 2-amino-2-deoxy-D-galactose, and D-galacturonic acid. The presence of fatty acyl groups has not been demonstrated the protein portion may confer some hydrophobic properties on the complex. 

R" = -H, 5-0-carbamoyl-2-amino-2-deoxy-L-xylonic acid or the 3-deoxy derivative... 

Many pyrazine and quinoxaline syntheses yield mono- or di-N-oxides (76H(4)769). The condensation of a-aminooximes with 1,2-diketones results in the direct formation of pyrazine mono-N-oxides. The a-aminooximes themselves are not easily prepared but 2-amino-2-deoxy sugars readily form the oximes, which have been condensed with glyoxal to yield the pyrazine 4-oxides (Scheme 18) (72JOC2635, 80JOC1693). 

An alternative approach to the use of a-aminoketones involves acetals (72JOC221) and pyrazine-2,3-diones have been synthesized by this route (Scheme 58). The acetals are readily available from the phthalimido derivatives via the a-chloroketones. Hemiacetals have also served as a starting point for pyrazine synthesis, although in most cases hemiacetals are too labile to be easily prepared examples are common in the 2-amino-2-deoxy sugar series 2-amino-2-deoxy-D-glucose for example dimerizes to the pyrazine (101) when generated in situ from the hydrochloride salt (68JAP6813469). 

Chemical Name 0-2,6-diamino-2,6-dideoxy-(3-L-idopyranosyl-(1- -3)-0-(3-D-ribofuranosyl-(1- -5)-0-[2-amino-2-deoxy-o -D-glucopyranosyl-(1- -4)I -2-deoxystreptamine... 

Amino 2 deoxy d glucose, conversion of hydrochloride to 2 acetamido-2 deoxy d glucose, 46, 2 l-(Ammomcthyl) cycloheptanol, 46, 31 2 Amino 2 methyl 1 propanol in isolation of levopimanc acid 45, 64 c-Amino p nitrobiphenyl, by nitration of o aminobiphenyl, 46, 86 from o,p dimtrobiphenyl, 46, 88 Amino 2 propanone, semicarbazone... 

Amino-sugars and Related Compounds. Part II. Observations on the Acidic Hydrolysis of Derivatives of 2-Amino-2-deoxy-D-glucose (D-Glucosamine), A. B. Foster, D. Horton, and M. Stacey,... 

Amino-2-deoxy-a-D-glucose (a-D-Glucosamine) from Crustacean Shell, M. Stacey and J. M. Webber, Methods Carbohydr. Chem., 1 (1962) 228-230. 

Note. The alternative name using a substituent prefix (see 2-Carb-35.1) is 3,4,6-tri-0-acetyl-2-amino-2-deoxy-l-0,2-N-[(methylamino)methylylidene]-a-D-glucopyranose. 

Lactosediamine (LacdiN) 2-Amino-2-deoxy-P-D-galactopyranosyl-(1 -44)-D-glucosamine... 

Isolated chitins are highly ordered copolymers of 2-acetamido-2-deoxy-/3-D-glucose and 2-amino-2-deoxy-j6-D-glucose. The occurrence of the latter is explained by the fact that in vivo chitin is covalently finked to proteins via the nitrogen atom of approximately one repeating unit out of ten, therefore upon isolation a degree of deacetylation close to 0.10 is found. Chito-biose, 0-(2-amino-2-deoxy-j6-D-glucopyranosyl)-(l 4)-2-amino-2-deoxy-... 

CN 0-2-amino-2-deoxy-a-D-glucopyranosyl-(l—>4)-0-[0-2,6-diamino-2,6-dideoxy-p-l-idopyranosyl(l->3)-... 

Compound 278 was convertible into 2-amino-2-deoxy- (280) and 2,7-diamino-2,7-dideoxy-a-DL-carba-glucopyranose (281) derivatives in satisfactory yields. 

Sharpless reaction of the enantiomeric alkenes (47) produced the precursors for 2-amino-2-deoxy-o -D and -L-carba-glucopyranoses. These compounds were converted into the penta-7V,0-acetates by the following sequence. Replacement of the bromo group with an acetate ion, treatment with sodium in liquid ammonia, and peracetylation. 

Trehalosamine, 2-amino-2-deoxy-a-D-glucopyranosyl a-D-glucopy-ranoside (343), is an antibiotic produced by Streptomyces tavendulae. Four related compounds, the 3-amino-3-deoxy and 4-amino-4-deoxy isomers," ... 

Coupling of 237 with the protected 2-amino-2-deoxy-o -D-glucopyranosyl bromide (348) in dichloromethane in the presence of silver triflate afforded a diastereoisomeric mixture. The isomer related to the natural one was depro-tected with sodium in liquid ammonia, to give the carba-trehalosamine... 

As 2-amino-2-deoxy-D-mannose is tumorstatic and 2-acetamido-2-deoxy-D-mannose 6-phosphate is an obligatory intermediate in the biosynthetic pathway to sialic acid, displacement of the essential OH-6 with a fluorine atom should be interesting from the biological viewpoint. 2-Acetamido-1,3,4-tri-0-acetyl-2,6-dideoxy-6-fluoro-D-mannopyranose (see Table 111 in Section 11,3) and its O- and A,0-deacetyl derivatives were prepared the first compound showed weak anticancer activity. 

A monoaminopentose, 4-amino-4-deoxy-L-arabinose, is known as a component of some Gram-negative bacteria. It is linked, as the )5-pyranosyl phosphate (18), to a 2-amino-2-deoxy-y -D-glucopyranosyI residue in the lipid A part of the LPS. ... 

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