Aminocyclitol Antibiotics by Kenneth L. Rinehart, Jr. and Tetsuo Suami (Eds.)

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By Kenneth L. Rinehart, Jr. and Tetsuo Suami (Eds.)

content material: Aminocyclitol antibiotics : an advent / Kenneth L. Rinehart, Jr. and Lois S. guard --
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 constructions of diastereomers of dihydrospectinomycins / Louise Foley and Manfred Weigele --
Chemical amendment of aminoglycosides : a unique 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 constructions of teenage elements of the fortimicin advanced / 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. put up, J.H. Seely, and J. Tadanier --
The constructions of latest 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 workforce --
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 concerning 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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In 1969, Rinehart and his coworkers first prepared modified antibiotics named "Hybrimycins" by a newly devised technique of bioconversion (1,2,3). The hybrimycins are neomycin analogs in which an amino-cyclitol moiety of neomycin, 2-deoxystreptamine, has been replaced by streptamine (scyllo-inosadiamine-1,3) or 2-epistreptamine (myoinosadiamine-1,3). This bioconversion is now called "mutasynthesis" and is used widely as a powerful tool for a preparation of new antibiotics. The investigations on hybrimycins stimulated us to initiate a study on a preparation of modified antibiotics that have other aminocyclitols rather than 2-deoxystreptamine in a 2-deoxystreptamine containing antibiotics.

N u c l e o p h i l i c opening of the epoxide r i n g by an acetate i o n , followed by aqueous barium hydroxide h y d r o l y s i s gave 5,6-diepineamine (LL) i n 22% y i e l d , and neamine, G was a l s o recovered i n 10% y i e l d (14) ( F i g . 12). These epineamines were t e s t e d against s e v e r a l microorganisms. Only 5-epineamine, GG showed a hopeful r e s u l t against a r e s i s t a n t s t r a i n of b a c t e r i a , but 6-epineamine, J J and 5,6-diepineamine, LL d i d not show any improvement of the a c t i v i t y against a r e s i s t a n t s t r a i n of b a c t e r i a , moreover they showed a marked decrease of the a c t i v i t y against o r d i n a r y b a c t e r i a , compared t o the parent neamine, G (Table 3) (14).

Tsuchiya, T. , Bull. Chem. Soc. , (1972), 45, 2847. 33. Umezawa, H . , Tsuchiya, T . , Muto, R. , Bull. Chem. Soc. , (1972), 45, 2842. 34. , Okazaki, Y. and Tsuchiya, T . , Bull. Chem. Soc. , (1972), 45, 3619. 35. Tipson, R. S. , Carbohyd. , (1965), 1, 338. 36. , Horton, D. and Tsuchiya, T . , Carbohyd. , (1966), 2, 349. 37. Jikihara, T . , Tsuchiya, T . , Umezawa, S. , Bull. Chem. Soc. , (1973), 46, 3507. 38. , Umezawa, H . , Okazaki, Y. and Tsuchiya, T . , Bull. Chem. Soc. , (1972), 45, 3624.

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