KEGG   ENZYME: 4.2.3.152
Entry
EC 4.2.3.152                Enzyme                                 

Name
2-epi-5-epi-valiolone synthase;
AcbC;
ValA;
CetA;
SalQ;
C7-cyclitol synthase
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
Sysname
alpha-D-sedoheptulopyranose-7-phosphate phosphate-lyase (cyclizing; 2-epi-5-epi-valiolone-forming)
Reaction(IUBMB)
alpha-D-sedoheptulopyranose 7-phosphate = 2-epi-5-epi-valiolone + phosphate [RN:R10937]
Reaction(KEGG)
R10937
Substrate
alpha-D-sedoheptulopyranose 7-phosphate [CPD:C20956]
Product
2-epi-5-epi-valiolone [CPD:C17691];
phosphate [CPD:C00009]
Comment
The enzyme is highly specific for alpha-D-sedoheptulopyranose 7-phosphate. It requires a divalent metal ion (Zn2+ or Co2+) and an NAD+ cofactor, which is transiently reduced during the reaction. The enzyme is involved in the biosynthesis of C7N-aminocyclitol natural products, such as the valienamine moiety of the antidiabetic drug acarbose and the crop protectant validamycin A. cf. EC 4.2.3.155, 2-epi-valiolone synthase and EC 4.2.3.154, demethyl-4-deoxygadusol synthase.
History
EC 4.2.3.152 created 2015, modified 2016
Pathway
ec00525  Acarbose and validamycin biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K19969  2-epi-5-epi-valiolone synthase
Genes
SERA: Ser39006_003950
SERQ: CWC46_03950
RHD: R2APBS1_3641
PFC: PflA506_4591
PEZ: HWQ56_09190
PAEW: KIH87_05110
CJA: CJA_3250
GPB: HDN1F_13870(acbC)
CVC: BKX93_19945
BTZ: BTL_4163
BOK: DM82_5622
SUR: STAUR_1386(gacC)
CBB: CLD_3207
MMI: MMAR_0578(aroB_1)
MMAE: MMARE11_05350(aroB_1)
MHAD: B586_06435
MLJ: MLAC_02190(aroB_1)
NAD: NCTC11293_02222(aroB_1)
RER: RER_54360
REY: O5Y_25890
RHB: NY08_95
RHS: A3Q41_04747(aroB_3)
SRT: Srot_2448
SHY: SHJG_0276
SALS: SLNWT_0595
SGU: SGLAU_01035(gacC)
STRM: M444_32560
SRW: TUE45_05037(aroB_3)
SLE: sle_45870(sle_45870)
SFK: KY5_0702
SRJ: SRO_6646
SGF: HEP81_06989(gacC)
SCYG: S1361_01415(aroB2)
SAUH: SU9_022190
FAL: FRAAL4639
AOI: AORI_5447(aroB)
AORI: SD37_10235
SESP: BN6_52640
ACTI: UA75_21530
ACAD: UA74_21050
SAQ: Sare_2489
ASE: ACPL_3680(acbC) ACPL_6250
CWO: Cwoe_1465
 » show all
Reference
1  [PMID:10196166]
  Authors
Stratmann A, Mahmud T, Lee S, Distler J, Floss HG, Piepersberg W
  Title
The AcbC protein from Actinoplanes species is a C7-cyclitol synthase related to 3-dehydroquinate synthases and is involved in the biosynthesis of the alpha-glucosidase inhibitor acarbose.
  Journal
J Biol Chem 274:10889-96 (1999)
DOI:10.1074/jbc.274.16.10889
  Sequence
[ase:ACPL_3680]
Reference
2  [PMID:16151088]
  Authors
Yu Y, Bai L, Minagawa K, Jian X, Li L, Li J, Chen S, Cao E, Mahmud T, Floss HG, Zhou X, Deng Z
  Title
Gene cluster responsible for validamycin biosynthesis in Streptomyces hygroscopicus subsp. jinggangensis 5008.
  Journal
Appl Environ Microbiol 71:5066-76 (2005)
DOI:10.1128/AEM.71.9.5066-5076.2005
  Sequence
[shy:SHJG_0276]
Reference
3  [PMID:17195255]
  Authors
Wu X, Flatt PM, Schlorke O, Zeeck A, Dairi T, Mahmud T
  Title
A comparative analysis of the sugar phosphate cyclase superfamily involved in primary and secondary metabolism.
  Journal
Chembiochem 8:239-48 (2007)
DOI:10.1002/cbic.200600446
  Sequence
Reference
4  [PMID:18648803]
  Authors
Choi WS, Wu X, Choeng YH, Mahmud T, Jeong BC, Lee SH, Chang YK, Kim CJ, Hong SK
  Title
Genetic organization of the putative salbostatin biosynthetic gene cluster including the 2-epi-5-epi-valiolone synthase gene in Streptomyces albus ATCC 21838.
  Journal
Appl Microbiol Biotechnol 80:637-45 (2008)
DOI:10.1007/s00253-008-1591-2
  Sequence
[sals:SLNWT_0595]
Reference
5  [PMID:24832673]
  Authors
Kean KM, Codding SJ, Asamizu S, Mahmud T, Karplus PA
  Title
Structure of a sedoheptulose 7-phosphate cyclase: ValA from Streptomyces hygroscopicus.
  Journal
Biochemistry 53:4250-60 (2014)
DOI:10.1021/bi5003508
  Sequence
[shy:SHJG_0276]
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.152
IUBMB Enzyme Nomenclature: 4.2.3.152
ExPASy - ENZYME nomenclature database: 4.2.3.152
BRENDA, the Enzyme Database: 4.2.3.152

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