Kanamycin 3 -deoxy

Deoxy-2,3-0-isopropylidene-/ -D-fhreo-hexulo-5-enofuranose 130, 6-Deoxy-2,3-0-isopropylidene-/ -D-arabino-hexuto furanose. . 131, 6-Deoxy kanamycin. ... 

Preparation of several fluorinated analogs of kanamycin A (673) were reported. 6"-Deoxy-6"-fluorokanamycin A (674) was prepared through... 

This enzyme [EC 2.7.7.46] catalyzes the reaction of a nucleoside triphosphate with gentamicin to produce a 2"-nucleotidylgentamicin and pyrophosphate (or, diphosphate). The nucleoside triphosphate can be ATP, dATP, CTP, ITP, or GTP. Kanamycin, tobramycin, and sisomicin can also act as the acceptor substrate. The nucleotidyl residue is transferred to the 2-hydroxyl group of the 3-amino-3-deoxy-D-glucose moiety in the acceptor substrate. 

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]. 

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... 

T. Tsuchiya and S. Umezawa, Studies of antibiotics and related substances. XXI. The synthesis of deoxy and chlorodeoxy derivatives of kanamycin, Bull. Chem. Soc. Jpn. 38 1181 (1965). 

T. Tsuchiya and S. Umezawa, Studies of antibiotics and related substances. XXI. The synthesis of deoxy and chlorodeoxy derivatives of kanamycin. Bull. Chem. Soc. Jpn. 38 1181 (1965). T, Suami, L. Hough, M. Tsuboi, T. Machinami, and N. Watanabe, Molecular mechanisms of sweet taste. V. Sucralose and its derivatives, J. Carbohydr. Chem. 73 1079 (1994). 

Deoxykanamycin A, an antibiotic resistant to 3 -phosphotransferase-modifying enzymes [(APH)3 -la s], has been prepared via two different routes. One route used Barton s deoxygenation protocol [87], and in another a mixture of 2, 3 - and 3, 4 -epoxy intermediates of kanamycin A derivatives resulted in the formation of a single product (3 -deoxy derivative) upon reduction with Raney nickel or sodium borohydride [88]. 

A number of kanamycin analogs, including 3 -deoxy-2 -e/ i-kanamycin A [90], 5-deoxy-, 5,4 -dideoxy-, 5-deoxy-5-epi-chloro-, and 5,4 -dideoxy-5,4 -di-epi-chlo-rokanamycin A [91], as well as 3 -deoxykanamycin B (tobramycin) [92], were prepared and tested against several sensitive and resistant organisms. Antibacterial activity data profile revealed that deoxygenation of kanamycin at the 5-position results in the loss of activity and that the 4 -epichlorination of kanamycin A results in lack of activity. 

Several other kanamycin A analogs, including 4"-e/7i-kanamycin A together with 4",5"-unsaturated, and 3",4"-cyclic urethane by products [104], 4"-deoxy-4",5"-didehydro, and 4"-deoxy-5"-e/7i-kanamycin A [105], as well as a number of 4"-epi-analogs (OH, F, N3) of amikacin [106] have also been prepared, all of which are much less active than the parent antibiotics. 

The same group has also synthesized a number of 4"-epi-kanamycin A analogs, including 4",6"-dideoxy-4",6"-difluoro-, 4",6"-dideoxy-4"-fluoro-, 6"-deoxy-6"-fluoro-,... 

The same group also has described the syntheses of 6"-deoxy-6"-fluorokana-mycin A, 6"-deoxy-6"-fluoroamikacin, and l-A-[(/ )- and (/ 5 )-3-amino-2-fluoropro-panoyl] kanamycin A, using the DAST reagent for fluorination of the corresponding hydroxyl groups of kanamycin A and amikacin derivatives [112],... 

A series of halogenated analogs of kanamycins, including 3, 4, 6 -trideoxy-6 -fluorokanamycin C (218), 3, 4 -dideoxy-6 -C-fluoromethyl kanamycin B [114], 6"-chloro-6"-deoxyamikacin (202) and some of its derivatives [115], as well as 3 -deoxy-3 -fiuorokanamycin A (219) and its 3, 4 -dideoxy-3 -fluoro analog 220 [45] were also prepared by the same research group. Antibacterial activity results showed weak activity for 6 -fluoro, moderate activity for 6 -fluoromethyl, and good activity (better than the parent antibiotics) for 3 -fluoro derivatives. 

A few other fluorinated kanamycins, including 5-deoxy-5-epi-fluoroamikacin, 5-deoxy-5-ep(-fluoroarbekacin, and their related analogs, have been prepared to study the fluorination-toxicity relationship. In contrast to the low toxicities of the 5-fluoro derivatives [121], these epi-fluoro compounds showed acute toxicity values identical to those of arbekacin and amikacin [122]. This indicates the importance of stereo-electronic effects of the fluoro group at position 5 of the 2-deoxystreptomine moiety in toxicity of aminoglycoside antibiotics. 

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