Glucopyranosyl antibiotics

D4 25 Protein synthesis Glucopyranosyl antibiotics Streptomycin Bactericide... 

HI 26 Trehalase and inositol synthesis Glucopyranosyl antibiotics Validamycin Specific for rice sheath blight Rhizoctonia solani)... 

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," ... 

The Mukaiyama condensation method was also utilized in the synthesis of several antibiotics and related bioactive substances. These syntheses include apramycin, using 4-azido-2,3,6-tri-(P-benzyl-4-deoxy-) -D-glucopyranosyl fluoride (prepared from the corresponding a-D-glucopyranosyl chloride by the AgF method ) avermectin B , using protected sugar derivatives of oleandrosyl fluoride (a-L-Ole-F) and 0-(a-L-01e)-(1 4)-a-L-0le-F (both... 

Neomycin Neomycin is a complex of aminoglycoside antibiotics (neomycin A, neomycin B, and neomycin C) that is synthesized by the actinomycete Streptomyces fradiae. [26-30]. For example, neomycin B is 0-2,6-diamino-2,6-didesoxy-a-D-glucopyranosyl-(l )-0-[0-2,6-diamino-2,6-didesoxy-)3-L-idopyranosyl(l—>3)-)3-D-ribofuranosyl-(l— 5)]-2-desoxy-D-streptamine (20.3.1). 

Kanamycin Kanamycin, 0-3-amino-3-deoxy-a-D-glncopyranosyl-(l—>6)-0-[6-deoxy-6-amino-a-D-glucopyranosyl-(l—>4)]-2-deoxy-D-streptamine (3.4.6), is isolated from a cultnre liquid of the actinomycete S. kanamyceticus, which produces three antibiotics— kanamycines A, B, and C [259-262]. 

Fermentation procedures for preparing uridine 5 -(2-acetamido-2-deoxy-a-D-glucopyranosyl pyrophosphate) have also been reported. One of them255 involves the cultivation of Helminthosporium sativum in the presence of 2-amino-2-deoxy-D-glucose and the antibiotic polyoxin the latter is an inhibitor of chitin biosynthesis. The other256 utilized the incubation of yeast cells with uridine 5 -phosphate in the presence of an excess of 2-amino-2-deoxy-D-glucose and inorganic phosphate.257... 

The antibiotic kanamycin is chemically related to streptomycin, as it is 4-0-(6-amino-6-deoxy-a-D-glucopyranosyl)-6-0-(3-amino-3-deoxy-a-D-glucopyranosyl)-2-deoxystreptamine. Two isomorphous crystalline compounds, namely, kanamycin monosulfate monohydrate and kanamycin monoselenate monohydrate, were used in elucidating... 

Antibiotic X-14847 (compound 98 see pg. 321), produced by Micromonospora echinospora, has been identified at l-0-(2-amino-2-deoxy-a-D-glucopyranosyl)-D-myo-inositol showing weak antibiotic activity [96],... 

Trichostatin A (38a) is a ( , )-A -hydroxy-7-oxo-2,4-heptadienamide isolated from some strains of Streptomyces hydroscopicus and is an antifungal antibiotic [65] as well as a potent inhibitor of mammalian histone deacetylase used in cancer chemoprevention. Two other metabolites with similar biological activity have also been isolated trichostatin B (38b), which is the corresponding ferric chelate [65] and trichostatin C (38c), a glucopyranosyl derivative [66]. 

Paromamine, neamine, 4-0-(6-amino-6-deoxy- -D-glucopyranosyI)-2-deoxystreptamine, 5-0- (2-amino-2-deoxy-o-D-glucopyranosyl) -2-deoxy-streptamine, kasugamycin, and a,a-trehalosamine have been synthesized. A common feature in the structures of these antibiotics is the presence of an a-o-glycosidic linkage. In the total syntheses, modified Koenigs-Knorr reactions, or addition of nitrosyl chloride " to an enose, were successfully used. 

As a related glycoside, 4-0-(6-amino-6-deoxy-/S-D-glucopyranosyl)-3-0-methyl-( + )-inositol was synthesized however, it showed no antibiotic activity. ... 

C11H14N4O4, Mr 266.26, cryst., mp. 247°C (decomp.), cytotoxic nucleoside antibiotic from Streptomyces tu-bercidicus, LD50 (rat p. o.) 16 mg/kg, with antitumor, antifungal, and antiviral activities. T. was also isolated as one of the main cytotoxins from Tolypothrix bys-soidea. Known derivatives of T. are the 5 -0-sulf-amoyl compound (CnHisNsO S, Mr 345.34, herbicide) isolated from Streptomyces mirabilis as well as the cytotoxic and antifungal S -O-a-D-glucopyranosyl compound C,7H24N40, Mr 428.40, [aJo +10° (HjO) isolated from Plectonema radiosum and Tolypothrix distorta. 

Cladinose analogues of 16-membered macrolide antibiotics have been prepared. Ethyl P-L-cladinoside was produced by ethanolysis of erythromycin A, and, after alkylation at 0-4, the alkylated products were linked to 0-4 of the mycaminose residue to give 3"-O-methyl-4"-0-alkyl derivatives of 9-dehydro-3-0-propionyl-leucomycin V. Microbial glycosylation by a strain of Streptomyces hygroscopicus has been used to make the 2 -0-P-D-glucopyranosyl derivatives of erythromycin B, erythromycin A oxime and azithromycin. ... 

---