ArticleBiochemistry2007
Molecular architecture of DesI: a key enzyme in the biosynthesis of desosamine.
Article in Biochemistry, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 38 citations in OpenAlex.
- Compressing Chemistry Reveals Functional Groups.Journal of chemical information and modeling · 2026Article
- Insights into the biosynthesis of septacidin l-heptosamine moiety unveils a VOC family sugar epimerase.Acta pharmaceutica Sinica. B · 2023Article
- Characterization of an aminotransferase from Acanthamoeba polyphaga Mimivirus.Protein science : a publication of the Protein Society · 2021Article
- Biosynthetic access to the rare antiarose sugarChemical science · 2020Article
- Investigation of a sugar N-formyltransferase from the plant pathogen Pantoea ananatis.Protein science : a publication of the Protein Society · 2019Article
- The Mycobacterium tuberculosis complex has a pathway for the biosynthesis of 4-formamido-4,6-dideoxy-d-glucose.Protein science : a publication of the Protein Society · 2018Article
- Structural investigation on WlaRG from Campylobacter jejuni: A sugar aminotransferase.Protein science : a publication of the Protein Society · 2017Article
- Structure of the external aldimine form of PglE, an aminotransferase required for N,N'-diacetylbacillosamine biosynthesis.Protein science : a publication of the Protein Society · 2015Article
- Structural Basis for the Stereochemical Control of Amine Installation in Nucleotide Sugar Aminotransferases.ACS chemical biology · 2015Article
- Structural characterization of AtmS13, a putative sugar aminotransferase involved in indolocarbazole AT2433 aminopentose biosynthesis.Proteins · 2015Article
- Three-dimensional structure of a sugar N-formyltransferase from Francisella tularensis.Protein science : a publication of the Protein Society · 2014Article
- The renaissance of bacillosamine and its derivatives: pathway characterization and implications in pathogenicity.Biochemistry · 2014Review
- The structural biology of enzymes involved in natural product glycosylation.Natural product reports · 2012Review
- Giant DNA virus mimivirus encodes pathway for biosynthesis of unusual sugar 4-amino-4,6-dideoxy-D-glucose (Viosamine).The Journal of biological chemistry · 2012Article
- Mechanisms and structures of vitamin B(6)-dependent enzymes involved in deoxy sugar biosynthesis.Biochimica et biophysica acta · 2011Review
- Biosynthetic enzymes of unusual microbial sugars.Current opinion in structural biology · 2010Review
- Structural analysis of WbpE from Pseudomonas aeruginosa PAO1: a nucleotide sugar aminotransferase involved in O-antigen assembly.Biochemistry · 2010Article
- Structural analysis of QdtB, an aminotransferase required for the biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-glucose.Biochemistry · 2009Article
- Increasing carbohydrate diversity via amine oxidation: aminosugar, hydroxyaminosugar, nitrososugar, and nitrosugar biosynthesis in bacteria.Current opinion in chemical biology · 2008Review
- Natural-product sugar biosynthesis and enzymatic glycodiversification.Angewandte Chemie (International ed. in English) · 2008Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found, for example, in such macrolide antibiotics as erthyromycin, azithromycin, and clarithromycin. The efficacies of these macrolide antibiotics are markedly reduced in the absence of desosamine. In the bacterium Streptomyces venezuelae, six enzymes are required for the production of dTDP-desosamine. The focus of this X-ray crystallographic analysis is the third enzyme in the pathway, a PLP-dependent aminotransferase referred to as DesI. The structure of DesI was solved in complex with its product, dTDP-4-amino-4,6-dideoxyglucose, to a nominal resolution of 2.1 A. Each subunit of the dimeric enzyme contains 12 alpha-helices and 14 beta-strands. Three cis-peptides are observed in each subunit, Phe 330, Pro 332, and Pro 339. The two active sites of the enzyme are located in clefts at the subunit/subunit interface. Electron density corresponding to the bound product clearly demonstrates a covalent bond between the amino group of the product and C-4' of the PLP cofactor. Interestingly, there are no hydrogen-bonding interactions between the protein and the dideoxyglucosyl group of the product (within 3.2 A). The only other sugar-modifying aminotransferase whose structure is known in the presence of product is PseC from Helicobacter pylori. This enzyme, as opposed to DesI, catalyzes amino transfer to the axial position of the sugar. A superposition of the two active sites for these proteins reveals that the major differences in ligand binding occur in the orientations of the deoxyglucosyl and phosphoryl groups. Indeed, the nearly 180 degrees difference in hexose orientation explains the equatorial versus axial amino transfer exhibited by DesI and PseC, respectively.
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