Streptamine 2,5-dideoxy

Variously derivatized 2-deoxy- and 2,5-dideoxy-streptamines have been synthesized 2,5-dideoxystreptamine was prepared from kanamycin by a simple procedure, and 5 0-(2,3-dideoxy-a-D-e 7r/iro-hexopyranosyl)-2-deoxy-strepta-mine dihydrochloride was obtained by glycosidation of a 2-deoxystreptamine derivative with tri-O-acetyl-D-glucal and hydrogenation. " The preparation of a 5-aminocyclohexanetetrol from kanamycin A is mentioned in Chapter 18. 

Suami s group has synthesized the isomeric 3,4-, 2,5-, 4,5-, and 4,6-dideoxy-streptamines using standard reactions of either azide ion or hydrazine on dideoxy-inositol sulphonates or oxirans. The reduction of l,2 3,4-dianhydroinositoIs and 1,2-anhydroinositol sulphonates with lithium aluminium hydride has furnished a series of dideoxy- or 1,4-anhydrodeoxy-inositols e.g., see Scheme 117), 1-Amino-1-deoxy-wyo-inositol has been synthesized by way of an azide displacement on 1l-1, 2 3,4-di-0-cyclohexylidene-5-0-methyl-6-0-toluene-/7-sul-phonyl-cA/ra-inositol. ... 

Chemical Name D-Streptamine, 0-3-amlno-3-deoxy-0t-D-glucopyranosyl-(1- 6)-O-[2,6-dl-amino-2,6-dideoxy-0t-D-glucopyranosyl-(1 4)]-2-deoxy sulfate (1 1)... 

Chemical Name 0-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-( 1->3)-0-(3-D-ribofuranosyl-(1->5)-0-[2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1->4)] -2-deoxy-D-streptamine... 

Simple analogs of an aminoglycoside antibiotic, 2,6-dideoxy-4-0- (671) and -5-0-(2,3-dideoxy-2-fluoro-o -D-r/Z>o-hexopyranosyl)streptamine (672) were prepared by coupling of tri-O-acetyl-2-fluoro-D-glucal (666) with cyclitol derivatives 668 or 667 (through 669 and 670) as shown. 

D-glucopyranosyl- (l->4) -0- [0-02, 6-diamino-2,6-dideoxy-3 L-o idopyranosy 1- (1+3) - 8-D-ribo-furanosyl-c (1+5)] -2-deoxy-D-streptamine. 

This enzyme [EC 2.1.4.2] catalyzes the reaction of arginine with l-amino-l-deoxy-xcyZ/o-inositol 4-phosphate to produce ornithine and l-guanidino-l-deoxy-scy//o-inositol 4-phosphate. Other substrates include lo-l-gua-nidino-3-amino-l,3-dideoxy-xcy//o-inositol 6-phosphate, streptamine phosphate and 2-deoxystreptamine phosphate. Canavanine can substitute for arginine. 

Neomycin Neomycin is a complex mixture of antibiotics (neomycins A, B, C, D, E, and F), that is formed by the actinomycete S. fradiae. Neomycin A, also called neamine, is 2-deoxy-4-0-(2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl)-D-streptamine (32.4.2), and it does not display antibiotic properties. At the same time, neomycin B, 0-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl(l— 4)-0-[0-2,6-diamino-2,6-dideeoxy-)3-L-idopyra-nosyl-(l—>3)-)3-D-ribofuranosyl-(l— 5)]-2-deoxy-D-streptamine (32.4.3), differs from neomycin A in the presence a second glycoside residue and exhibits powerful antibacterial... 

Paromomycin From a chemical point of view, paromomycin, 0-2-amino-2-deoxy-a-D-glucopyranosyl(l->4)-0-[0-2,6-diamino-2,6-dideoxy-j3-L-idopyranoxyl-(1 3)-j3-D-ribofuranosyl-(1 5)]-2-deoxy-D-streptamine (32.4.5), differs from neomycin B only in the replacement of the 6-amino group in the glucopyranosyl region of the molecule with a hydroxyl group, and it is isolated from a culture fluid of the actinomycete S. rimosus [256-258]. 

D-STREPTAMINE, 0-2,6-DIAMIN0-2,6-DIDEOXY-alpha-D-GLUCOPYRANDOSYL- (1 -4)-0-(beta-D-RIBOFURANDOSYL-(1-5))-2-DEOXY-... 

Paromomycin. 0-2-Amino-2-deoxy-a-D-giuco-pyranosyl-f l - 4)-0-[0-2,6-iiamino-2,6-tfideoxy-d-L-ido-pyranosyl-( l — 3)-3-D-ri o/uranosy/-(f — 5))-2-deo.iv-D. Streptamine O-2,6-diamin0-2,b-dideoxy-p -L -idopytttnosyf-(I — 3)-O-d-V-ribofuran0Syl-(l )-0-[2-omino-2-deoxy-i,-D-gtucopyranosyl- 4)]-2-deoxystreptamine paromomy-... 

Diamino-2,6-dideoxy-a-D-glucopyrano-syl-(l ->4)-[ -D-ribofuranosyl-(l - 5)]-2-deoxy-D-streptamine, SCI. Hetangmycin. SF 733. Antibiotic SF 733. Dekamycin IV [25546-65-0]... 

Umezawa s group has reported the synthesis of 4 -deoxy-kanamycin via the coupling of an appropriately derivatized 6-amino-4,6-dideoxy-D-x j /n-hexosyI chloride with a streptamine derivative. The enzymic phosphorylation and antibacterial activity of the modified antibiotic were examined. Ribostamycin has been converted into butirosin B and its 3, 4 -dideoxy derivative, thus formally... 

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