By Kenneth L. Rinehart, Jr. and Tetsuo Suami (Eds.)
content material: Aminocyclitol antibiotics : an advent / Kenneth L. Rinehart, Jr. and Lois S. protect --
Synthesis of aminocyclitol antibiotics / S. Umezawa --
amendment of aminocyclitol antibiotics / Tetsuo Suami --
Syntheses of some branched-chain aminocyclitol antibiotics / Juji Yoshimura, Masuo Funabashi, and Chung-Gi Shin --
a brand new synthesis of branched-chain epi-configuration deoxyhalogeno- and deoxyaminocyclitols / Donald E. Kiely and James M. Riordan --
The stereospecific synthesis of spectinomycin / D.R. White, R.D. Birkenmeyer, R.C. Thomas, S.A. Mizsak, and V.H. Wiley --
Synthesis of spectinomycin analogs / R.C. Thomas, D.R. White, V.H. Wiley, and D.A. Forster --
Spectinomycin amendment / W. Rosenbrook, Jr. and Ronald E. Carney --
The buildings of diastereomers of dihydrospectinomycins / Louise Foley and Manfred Weigele --
Chemical amendment of aminoglycosides : a singular synthesis of 6-deoxyaminoglycosides / Barney J. Magerlein --
The impression of O-methylation at the job of aminoglycosides / J.B. McAlpine, R.E. Carney, R.L. Devault, A.C. Sinclair, R.S. Egan, M. Cirovic, R. Stanaszek, and S. Mueller --
The synthesis and organic houses of 3'- and 4'-thiodeoxyneamines and 4'-thiodeoxykanamycin B / Thomas W. Ku, Robert D. Sitrin, David J. Cooper, John R.E. Hoover, and Jerry A. Weisbach --
Synthesis of analogs of kanamycin B / J.P.H. Verheyden, D.B. Repke, T.C. Tompkins, and J.G. Moffatt --
The selective N-acylation of kanamycin A / M.J. Cron, J.G. Keil, J.S. Lin, M.V. Ruggeri, and D. Walker --
Carbon-13 NMR spectra of aminoglycoside antibiotics / Takayuki Naito, Soichiro Toda, Susumu Nakagawa, and Hiroshi Kawaguchi --
The buildings of stripling elements of the fortimicin complicated / J.B. McAlpine, R.S. Egan, R.S. Stanaszek, M. Cirovic, S.L. Mueller, R.E. Carney, P. Collum, E.E. Fager, A.W. Goldstein, D.J. Grampovnik, P. Kurath, J.R. Martin, G.G. submit, J.H. Seely, and J. Tadanier --
The buildings of recent fortimicins having double bonds of their purpurosamine moieties / Kunikatsu Shirahata, Gen Shimura, Seigo Takasawa, Takao Iida, and Keiichi Takahashi --
Enzymes editing aminocyclitol antibiotics and their roles in resistance choice and biosynthesis / Julian Davies --
Biosynthesis and mutasynthesis of aminocyclitol antibiotics / Kenneth L. Rinehart, Jr. --
Chemical and organic amendment of antibiotics of the gentamicin crew --
P.J.L. Daniels, D.F. Rane, S.W. McCombie, R.T. Testa, J.J. Wright, and T.L. Nagabhushan --
Synthesis and mutasynthesis of pseudosaccharides on the topic of aminocyclitol-glycoside antibiotics / J. Cléophax, A. Roland, C. Colas, L. Castellanos, S.D. Géro, A.M. Sepulchre, and B. Quiclet --
a number of interactions of aminoglycoside antibiotics with ribosomes / Bernard D. Davis and Phang-C. Tai.
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Extra info for Aminocyclitol Antibiotics
Bull. Chem. Soc. , (1969), 42, 533. , Nishimura, Y. and Tsumura, T . , J. Antibiot. (Tokyo), (1968), 21, 424. , Nishimura, Y. and Tsumura, T . , Bull. Chem. Soc. , (1969), 42, 537. , Tatsuta, K. and Tsumura, T . , J. Antibiot. (Tokyo), (1968), 21, 162. , Tatsuta, K. and Tsumura, T . , Bull. Chem. Soc. , (1969), 42, 529. , Tsuchiya, T . , Umezawa, S. , J. Antibiot. (Tokyo), (1972), 25, 741. Takagi, Y . , Miyake, T . , Tsuchiya, T . , Umezawa, S. , J. Antibiot. (Tokyo), (1973), 26, 403. Evans, M.
Ch002 f fl f f f f f fl ? ch002 00 Nal-Zn^ DMF NHTs \ Nal/DMF TsHN ,0 NHTs "QV VQ 3 2 Dibekacin ( MM ) Figure 13. (VV) (WW) Amikacin Butirosin Β Figure 14. 2. UMEZAWA 33 Synthesis of Aminocyclitol Antibiotics i n h i b i t s almost a l l i n a c t i v a t i o n s by phosphotransferases, a d e n y l y I t r a n s f e r a s e s , and a c e t y l t r a n s f e r a s e s . Thus, a combi n a t i o n of deoxygenation, 1 - N - a c y l a t i o n , and 6 -N-methylation provides s i g n i f i c a n t a c t i v i t y against v a r i o u s r e s i s t a n t orga nisms.
The p-methylbenzylidene and THP groups were removed by h y d r o l y s i s w i t h aqueous a c e t i c a c i d t o give LLL. F i n a l l y , treatment of LLL w i t h sodium metal i n l i q u i d ammonia simultaneously removed the dimethylsulfamoyloxy group and the t o s y l and benzyloxycarbonyl groups, g i v i n g the 3"-deoxydihydrostreptomycin (MMM), which was i d e n t i c a l w i t h the authen t i c specimen obtained by a t o t a l s y n t h e s i s i n a l l r e s p e c t s . I n c o n c l u s i o n , the s y n t h e t i c s t u d i e s d i r e c t e d towards amino c y c l i t o l a n t i b i o t i c s now cover a wide area, and we have a great number of r e f e r e n c e s , which, i n c l u d e s , f o r i n s t a n c e , extensive s t u d i e s on gentamicins by Daniels and a s s o c i a t e s of the Schering Corporation.
Aminocyclitol Antibiotics by Kenneth L. Rinehart, Jr. and Tetsuo Suami (Eds.)