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Literature summary for 5.1.3.35 extracted from

  • Zhang, C.S.; Stratmann, A.; Block, O.; Brückner, R.; Podeschwa, M.; Altenbach, H.J.; Wehmeier, U.F.; Piepersberg, W.
    Biosynthesis of the C(7)-cyclitol moiety of acarbose in Actinoplanes species SE50/110. 7-O-Phosphorylation of the initial cyclitol precursor leads to proposal of a new biosynthetic pathway (2002), J. Biol. Chem., 277, 22853-22862.
    View publication on PubMed
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Cloned(Commentary)

Cloned (Comment) Organism
gene acbO, encoded in the acbKMLNOC operon, DNa and amino acid sequence determination and analysis, overexpression of N-terminally His-tagged enzyme in Streptomyces lividans strain TK64, expression in Escherichia coli is not successful, method development, overview Actinoplanes sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2-epi-5-epi-valiolone 7-phosphate Actinoplanes sp.
-
 5-epi-valiolone 7-phosphate
-
 r

Organism

Organism UniProt Comment Textmining
Actinoplanes sp. Q8RMD1 gene acbO
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-epi-5-epi-valiolone 7-phosphate
-
 Actinoplanes sp. 5-epi-valiolone 7-phosphate
-
 r
2-epi-5-epi-valiolone 7-phosphate 2-epimerisation Actinoplanes sp. 5-epi-valiolone 7-phosphate product identification by TLC analysis, overview r

Synonyms

Synonyms Comment Organism
AcbO
-
 Actinoplanes sp.

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
 assay at Actinoplanes sp.

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.6
-
 assay at Actinoplanes sp.

General Information

General Information Comment Organism
metabolism the enzyme is involved in the acarbose biosynthesis, pathway overview. The biosynthesis of the C7-cyclitol, called valienol (or valienamine), of the alpha-glucosidase inhibitor acarbose starts from the cyclization of sedo-heptulose 7-phosphate to 2-epi-5-epivaliolone. Synthesis of the intermediate 2-epi-5-epi-valiolone is catalyzed by the cyclase AcbC encoded in the biosynthetic (acb) gene cluster of Actinoplanes sp. SE50/110. The cyclitol precursor 2-epi-5-epi-valiolone is phosphorylated, forming the intermediate 2-epi-5-epi-valiolone 7-phosphate, by the enzyme AcbM as a first step in its conversion to the valienol moiety. Epimerase AcbO catalyzes the next conversion step, leading to an isomeric phosphorylated substance with the same molecular mass, most likely the epimerization product of 2-epi-5-epivaliolone 7-phosphate to 5-epi-valiolone 7-phosphate Actinoplanes sp.