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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. safeguard --
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 singular synthesis of 6-deoxyaminoglycosides / Barney J. Magerlein --
The impact of O-methylation at the task 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 youngster parts 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. put up, J.H. Seely, and J. Tadanier --
The constructions 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 staff --
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 relating to 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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However, when the t r i - 0 - m e s y l d e r i v a t i v e (SS) was t r e a t e d w i t h sodium i o d i d e i n hot DMF without z i n c dust, i t a f f o r d e d the d e s i r a b l e 3',4'-unsaturated d e r i v a t i v e (UU) i n 92% y i e l d , which was a l s o l e d t o d i b e k a c i n (MM) by a s i m i l a r sequence of r e a c t i o n s i n a good y i e l d . The r o l e of z i n c dust as a determinant of a z i r i d i n e formation i s i n t e r e s t i n g . (See F i g u r e 13). Another important m o d i f i c a t i o n of a m i n o c y c l i t o l a n t i b i o t i c s was suggested by the presence of a p e c u l i a r aminoacyl r e s i d u e i n the s t r u c t u r e s of b u t i r o s i n s (VV) reported by the Parke-Davis researchers (42) i n 1971, because comparison o f b u t i r o s i n s w i t h r i b o s t a m y c i n i n d i c a t e d a remarkable e f f e c t of the L-4-amino-2h y d r o x y b u t y r y l s i d e chain ( c a l l e d HABA f o r short) , on the a n t i b a c t e r i a l s p e c t r a , i n h i b i t i n g kanamycin-resistant and - s e n s i t i v e b a c t e r i a over a wide range.

And Tsuchiya, T . , Bull. Chem. Soc. , (1971), 44, 1411. , Pure & Appl. 11/12, 1453 1476. Kumar, V. and Remers, W. , J. Org. , (1978), 43, 3327. Rinehart, K. L. Jr. , J. Amer. Chem. , (1963), 85, 1547. Umezawa, S. and Nishimura, Y . , J. Antibiot. (Tokyo), (1977), 30, 189. , Phostaki, I. and Zervas, L . , Chem. Ber. (1959), 92, 1288. Ferrier, R. J. , J. Chem. , (1965), 7429. , Advan. Carbohyd. Chem. , (1974), 30, 183 - 225. , Tsuchiya, T . , Muto, R. , J. Antibiot. (Tokyo), (1971), 24, 274. ch002 2.

Since an a n t i b i o t i c that has an α-D-glucopyranosyl moiety on the 5-0 of neamine was prepared by a t r a n s g l y c o s i d a t i o n r e a c t i o n w i t h neamine and maltose under the presence of an enzyme i n a b u f f ­ er s o l u t i o n (26) and t h i s a n t i b i o t i c was 2 t o 4 times more a c t i v e than the parent neamine, i t was i n t e r e s t i n g t o prepare i t s anomeric isomer: 5-0-(3-D-glucopyranosyl)neamine (DDD). Compound DDD was prepared from compound by the f o l l o w i n g r e a c t i o n process as shown i n F i g .

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