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 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 homes 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 juvenile 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. put up, J.H. Seely, and J. Tadanier --
The buildings of latest fortimicins having double bonds of their purpurosamine moieties / Kunikatsu Shirahata, Gen Shimura, Seigo Takasawa, Takao Iida, and Keiichi Takahashi --
Enzymes enhancing aminocyclitol antibiotics and their roles in resistance selection 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 regarding 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 resources for Aminocyclitol Antibiotics
3 1 6538P 0,,4 S. B. e u b t i l i a 6633 5-Amino-5-deoxyneamine 1 mg/ml) Neamine (Concentration: Compound Inactive. 5 - - _ 7 - • ML-1629 Table 4. ch003 ι I > g 2 ο ο 01 00 3. ) Ç CH CH NHCbe NHCbe J—O^ ) 2 V CH NHCbe 2 N H C be J~ ° v 3 NHCbe \NHCbe / AcO CbeNH CbeNH ftf CHa Figure 16. u CHa Reaction mechanism for the introduction of acetamido group CH NHCbe 2 Ν NHCbe CbeNH OH (UU) Figure 17. , P s e u d o t r i s a c c h a r i d e s were prepared by i n t r o d u c i n g another sugar t o the 5-0 or 6-0 p o s i t i o n , u s i n g compound J or Κ as a s t a r t ing m a t e r i a l .
Aureus Diameter activity eubtilie 31 mg/ml) B. Antimicrobial Neamine (1 Componud Table 1. ch003 ce 1 M a § i > 3. Modification of Aminocyclitol Antibiotics 47 But when compound _I was t r e a t e d heterogeneously w i t h Amberlite IR-120 (H+) i o n exchange r e s i n i n an aqueous acetone s o l u t i o n , a mixture o f three components was obtained. By a s i l i c a g e l column chromatography, the components were s u c c e s s f u l l y separated. These three components were a 6-0-acetyl d e r i v a t i v e ( J ) , 5-0-acetyl de r i v a t i v e (K) and the s t a r t i n g m a t e r i a l , H obtained i n 22, 25, and 21% y i e l d s , r e s p e c t i v e l y ( 5 ) ( F i g .
Ch002 2. UMEZAWA Synthesis of Aminocyclitol Antibiotics Figure 11. ch002 30 AMINOCYCLITOL ANTIBIOTICS Dibekacin (MM) (RR ) Figure 12. 2. UMEZAWA 31 Synthesis of Aminocyclitol Antibiotics of z i n c dust. The s y n t h e s i s began w i t h the p r o t e c t i o n of the amino groups of kanamycin Β w i t h t o s y l groups. Treatment of the penta-N-tosyl kanamycin Β (NN) w i t h cyclohexanone dimethyl k e t a l by the ketal-exchange procedure gave a mixture of 4",6"-0- and 3 ,4',4",6"-di-0-cyclohexylidene d e r i v a t i v e s , however, a d d i t i o n of about one h a l f e q u i v a l e n t of water as a 10% s o l u t i o n i n DMF to the r e a c t i o n mixture s e l e c t i v e l y removed the 3 ^ - c y c l o h e x y l i d e n e group to give the 4 ,6 -0-cyclohexylidene d e r i v a t i v e (00) i n 99% y i e l d .