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Literature summary 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

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.7.1.187 expression in Escherichia coli Actinoplanes sp.
2.7.1.188 expressed in strains of Streptomyces lividans 66 strains 1326, TK23, and TK64 Actinoplanes sp.
5.1.3.35 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)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.7.1.187 ATP + acarbose Actinoplanes sp.
-
 ADP + acarbose 7'''-phosphate
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolone Actinoplanes sp. the enzyme is involved in the biosynthesis of acarbose ADP + 2-epi-5-epi-valiolone 7-phosphate
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolone Actinoplanes sp. 50/110 the enzyme is involved in the biosynthesis of acarbose ADP + 2-epi-5-epi-valiolone 7-phosphate
-
 ?
5.1.3.35 2-epi-5-epi-valiolone 7-phosphate Actinoplanes sp.
-
 5-epi-valiolone 7-phosphate
-
 r

Organism

EC Number Organism UniProt Comment Textmining
2.7.1.187 Actinoplanes sp. Q8RMD4
-
-
2.7.1.188 Actinoplanes sp. Q8RIS8
-
-
2.7.1.188 Actinoplanes sp. 50/110 Q8RIS8
-
-
5.1.3.35 Actinoplanes sp. Q8RMD1 gene acbO
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.7.1.188 His-tagged AcbM protein Actinoplanes sp.

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.7.1.187 ATP + acarbose
-
 Actinoplanes sp. ADP + acarbose 7'''-phosphate
-
 ?
2.7.1.187 ATP + acarbose the enzyme does not use monomeric cyclitol precursors as substrates. No activity with 2-epi-5-epi-valiolone, 2-epi-5-epi-valiolol, 1-epi-2-epi-5-epi-valiolol, 1-epi-5-epi-valiolol, 5-epi-valiolol, 1-epi-valienol, valienol Actinoplanes sp. ADP + acarbose 7'''-phosphate
-
 ?
2.7.1.188 ATP + 1-epi-2-epi-5-epi-valiolol
-
 Actinoplanes sp. ?
-
 ?
2.7.1.188 ATP + 1-epi-2-epi-5-epi-valiolol
-
 Actinoplanes sp. 50/110 ?
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolol
-
 Actinoplanes sp. ?
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolol
-
 Actinoplanes sp. 50/110 ?
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolone
-
 Actinoplanes sp. ADP + 2-epi-5-epi-valiolone 7-phosphate
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolone the enzyme is involved in the biosynthesis of acarbose Actinoplanes sp. ADP + 2-epi-5-epi-valiolone 7-phosphate
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolone
-
 Actinoplanes sp. 50/110 ADP + 2-epi-5-epi-valiolone 7-phosphate
-
 ?
2.7.1.188 ATP + 2-epi-5-epi-valiolone the enzyme is involved in the biosynthesis of acarbose Actinoplanes sp. 50/110 ADP + 2-epi-5-epi-valiolone 7-phosphate
-
 ?
5.1.3.35 2-epi-5-epi-valiolone 7-phosphate
-
 Actinoplanes sp. 5-epi-valiolone 7-phosphate
-
 r
5.1.3.35 2-epi-5-epi-valiolone 7-phosphate 2-epimerisation Actinoplanes sp. 5-epi-valiolone 7-phosphate product identification by TLC analysis, overview r

Synonyms

EC Number Synonyms Comment Organism
2.7.1.187 AcbK
-
 Actinoplanes sp.
2.7.1.188 AcbM
-
 Actinoplanes sp.
5.1.3.35 AcbO
-
 Actinoplanes sp.

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
5.1.3.35 30
-
 assay at Actinoplanes sp.

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
5.1.3.35 7.6
-
 assay at Actinoplanes sp.

General Information

EC Number General Information Comment Organism
2.7.1.188 physiological function the enzyme is involved in the biosynthesis of acarbose Actinoplanes sp.
5.1.3.35 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.