Antibiotics sugar components

The high anti selectivity exhibited by the addition of organolithium reagents to 808 is exploited as a way of supplying two chiral centers for L-digitoxose (2,6-dideoxy-nZ o-hexose) (817), an antibiotic sugar component [226] (Scheme 109). 

The natural antibiotic novobiocin (Fig. 3) is an example of diversity enhancement by the combination of building blocks from different pathways, such as aromatic rings, isoprenoid, amino acid, and sugar components, finished by post-modification [22]. 

This conversion of readily available 2-furyl alcohols into unsaturated pyranosuloses proved a very effective route to racemic monosaccharides, through stepwise, selective functionalization of the enone grouping in 325. The shortest synthesis of a natural compound by following this scheme involves palladium-catalyzed hydrogenation of the aldosulose (325, R = Me) obtained from l-(2-furyl)ethanol, resulting209 in cinerulose A, the sugar component of the antibiotic cine-rubin. 

H. Grisebach, Biosynthesis of sugar components of antibiotic substances, Adv. Carbohydr. Chem. Biochem. 35 81 (1978). 

A 2,3,6-trideoxyhexose, namely, rhodinose (63), was shown to be the neutral sugar component in the antibiotic rhodomycin. 24 The structure was established by periodate oxidation, with isolation of acetaldehyde and... 

The Grignard reagent from (l-chloroethyl)dimethylphenylsilane, prepared in turn by a-methylation of (chloromethyl)dimethylphenylsilane, acts as a hydroxyethylating reagent after oxidative cleavage its use can be seen in a stereoselective synthesis124 of lincos-amine, the sugar component of the antibiotic lincomycin. 

In Chapter 32, Problem 3, we asked you to work out the stereochemistry of a sugar. One of the sugar components in the antibiotic kijanimycin has the gross structure and NMR spectrum shown below. What is its stereochemistry ... 

Instead of describing the biosynthesis of the individual sugar components of these antibiotics, it is advantageous to review the biosynthesis of the total molecule. A review on the biosynthesis of aminocyclitol ( aminoglycoside ) antibiotics has appeared.47... 

Nucleoside antibiotics contain a number of unusual sugar components. The chemistry, biosynthesis, and biochemistry of these antibiotics has been described in a book by Suhadolnik85 in which the literature is covered up to 1969. In Table II, significant results on the... 

Biosynthesis of Sugar Components from Nucleoside Antibiotics... 

Grisebach, Hans, Biosynthesis of Sugar Components of Antibiotic Substances, 35, 81-126... 

Antibiotic substances, biosynthesis of sugar components of, 35, 81-126 Antigens,... 

In an article that focuses particularly on some of the more-recent developments, Grisebach (Freiburg im Breisgau) discusses the biosynthesis of sugar components of antibiotic substances, a field that has shown major advances since the time of the article by Dutcher in Volume 18 of Advances. The chapter constitutes an integrating complement to the articles on aminocyclitol antibiotics by the Umezawas (Volume 30). 

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