PubMed · 14462181
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K LANGOWSKA, Z ROTH. 1962. [Muramic acid].. https://pubmed.ncbi.nlm.nih.gov/14462181/
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Deoxyaminosugars comprise an important class of deoxysugars synthesized by a variety of different microorganisms; they can be structural components of lipopolysaccharides, extracellular polysaccharides, and secondary metabolites such as antibiotics. Genes involved in the biosynthesis of the deoxyaminosugars are often clustered and are located in the vicinity of other genes required for the synthesis of the final compound. Most of the gene clusters for aminosugar biosynthesis have common features, as they contain genes encoding dehydratases, isomerases, aminotransferases, methyltransferases, and glycosyltransferases. In the present mini-review, the proposed biosynthetic pathways for deoxyaminosugar components of both macrolide and non-macrolide antibiotics are highlighted. The possibilities for genetic manipulations of the deoxyaminosugar biosynthetic pathways aimed at production of novel secondary metabolites are discussed.
[reaction: see text] L-Glycals can be prepared in seven steps from readily available D-glucals, enabling the facile construction of mirror-image carbohydrates such as the L-lactosamine derivative shown above.
Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions. [reaction: see text]