By Kenneth L. Rinehart, Jr. and Tetsuo Suami (Eds.)
content material: Aminocyclitol antibiotics : an creation / 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 buildings of diastereomers of dihydrospectinomycins / Louise Foley and Manfred Weigele --
Chemical amendment of aminoglycosides : a unique synthesis of 6-deoxyaminoglycosides / Barney J. Magerlein --
The impact 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 youngster 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 constructions of recent 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 decision and biosynthesis / Julian Davies --
Biosynthesis and mutasynthesis of aminocyclitol antibiotics / Kenneth L. Rinehart, Jr. --
Chemical and organic amendment of antibiotics of the gentamicin team --
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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Extra resources for Aminocyclitol Antibiotics
We have u s u a l l y used sodium h y d r i d e f o r the c y c l i z a t i o n , however, i n t h i s case, we used potassium t-butoxide on t r i a l and obtained higher y i e l d . The c y c l i c carbamate d e r i v a t i v e (FFF) was converted to i t s p-toluene s u l f onate s a l t and t r e a t e d w i t h dihydropyran i n the presence of p - t o l u e n e s u l f o n i c a c i d i n the u s u a l way t o g i v e a mixture of pert e t r a h y d r o p y r a n y l d e r i v a t i v e s (GGG) i n which t e t r a h y d r o p y r a n y l groups are introduced t o the h y d r o x y l and guanidino groups on the s t r e p t i d i n e p o r t i o n .
I should say a t t h i s p o i n t that t h i s t r a n s f o r m a t i o n took a great d e a l of work t o prepare a s u i t a b l y masked e n t i t y and, i n a d d i t i o n , t o f i n d out a s u i t a b l e deoxygenation r e a c t i o n . P a r e n t h e t i c a l l y h e r e , I w i l l mention a new deoxygenation r e a c t i o n which was a p p l i c a b l e t o the 3"-deoxygenation of d i h y d r o streptomycin. I n α-D-glucopyranosides, a d i f f i c u l t y l i e s i n the deoxygenation of secondary h y d r o x y l groups attached t o carbon atoms at which S 2 process i s hindered.
Figure 7. ch002 26 AMINOCYCLITOL ANTIBIOTICS chromatography w i t h s i l i c a g e l gave three f r a c t i o n s and one of them contained the d e s i r e d 3-L-glycoside. However, f u r t h e r s e p a r a t i o n from another product, which may be α-L-glycoside, was very troublesome, g i v i n g a v e r y poor y i e l d of the d e s i r e d pure g l y c o s i d e (EE). D e a c e t y l a t i o n of EE w i t h methanolic ammonia followed by treatment w i t h Dowex 1x2 (OH" form) i n aqueous acetone at room temperature f o r 2 hours gave FF.
Aminocyclitol Antibiotics by Kenneth L. Rinehart, Jr. and Tetsuo Suami (Eds.)