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
SERASer39006_003950
SERQCWC46_03950
RHDR2APBS1_3641
RTHLRK53_03190
PFCPflA506_4591
PEZHWQ56_09190
PAEWKIH87_05110
CJACJA_3250
GPBHDN1F_13870(acbC)
CVCBKX93_19945
BTZBTL_4163
BOKDM82_5622
COFFOZ74_00740
SURSTAUR_1386(gacC)
AVMJQX13_08230 JQX13_41180
CFUSCYFUS_007478
PAUUE8A73_036720
MEEDA075_19375
BBYCY96_27945
CBBCLD_3207
MMIMMAR_0578(aroB_1)
MMAEMMARE11_05350(aroB_1)
MHADB586_06435
MLJMLAC_02190(aroB_1)
NSRNS506_05945
NAHF5544_18765
NADNCTC11293_02222(aroB_1)
RERRER_54360
REYO5Y_25890
REBXU06_26170
RHBNY08_95
RHSA3Q41_04747(aroB_3)
RTMG4H71_11885
TSMASU32_10315
SRTSrot_2448
SHYSHJG_0276
SHOSHJGH_0110
SALSSLNWT_0595
SGUSGLAU_01035(gacC)
STRMM444_32560
SCZABE83_10155
SRWTUE45_05037(aroB_3)
SLEsle_45870(sle_45870)
SCLFBB341_29000
SLSSLINC_5104
SSIAA7J05_03495
SFKKY5_0702
SRJSRO_6646
SCYAEJ357_02100 EJ357_14575
SASTCD934_05045
SNQCP978_00070
SKACP970_39485
SGZC0216_19350
SRKFGW37_17500
SFICEIZ62_30660
SSPODDQ41_30765
SGFHEP81_06989(gacC)
SPACB1H29_04435
SCYGS1361_01415(aroB2)
SAUHSU9_022190
SROIIAG44_34870
STRYEQG64_25575
KITCFP65_6096
XYAET471_00715
CIRALFM56_12025
AERAERYTH_07130
NGVCDO52_07210
FALFRAAL4639
AOIAORI_5447(aroB)
AJAAJAP_35530
AMYCCU254_12845
AORISD37_10235
SESPBN6_52640
ACTIUA75_21530
ACADUA74_21050
STPStrop_2345
SAQSare_2489
MCABHXZ27_14335
ASEACPL_3680(acbC) ACPL_6250
ACTSACWT_3552 ACWT_6118
PLKCIK06_12685
PLABC6361_27335
PLATC6W10_29735
PRYPrubr_33290
CWOCwoe_1465
GLPGlo7428_0525
TSAAciPR4_1231
 » 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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