KEGG   ENZYME: 5.1.3.18
Entry
EC 5.1.3.18                 Enzyme                                 

Name
GDP-mannose 3,5-epimerase;
GME (gene name);
GDP-D-mannose:GDP-L-galactose epimerase;
guanosine 5'-diphosphate D-mannose:guanosine 5'-diphosphate L-galactose epimerase
Class
Isomerases;
Racemases and epimerases;
Acting on carbohydrates and derivatives
Sysname
GDP-alpha-D-mannose 3,5-epimerase
Reaction(IUBMB)
(1) GDP-alpha-D-mannose = GDP-beta-L-galactose [RN:R00889];
(2) GDP-alpha-D-mannose = GDP-beta-L-gulose [RN:R07672]
Reaction(KEGG)
R00889 R07672
Substrate
GDP-alpha-D-mannose [CPD:C00096]
Product
GDP-beta-L-galactose [CPD:C02280];
GDP-beta-L-gulose
Comment
The enzyme catalyses the formation of the stable intermediate GDP-beta-L-gulose as well as GDP-beta-L-galactose. The reaction proceeds by C4' oxidation of GDP-alpha-D-mannose followed by epimerization of the C5' position to give GDP-beta-L-4-dehydro-gulose. This intermediate is either reduced to give GDP-beta-L-gulose or the C3' position is epimerized to give GDP-beta-L-4-dehydro-galactose, followed by C4' reduction to yield GDP-beta-L-galactose. Both products serve as intermediates in two different variants of plant L-ascorbate biosynthesis pathways.
History
EC 5.1.3.18 created 1986, modified 2020
Pathway
ec00053  Ascorbate and aldarate metabolism
ec00520  Amino sugar and nucleotide sugar metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K10046  GDP-D-mannose 3', 5'-epimerase
Genes
ATH: AT5G28840(GME)
ALY: 9308399
CRB: 17883756
CSAT: 104707129 104736843 104771306
EUS: EUTSA_v10004408mg
BRP: 103854620 103874594(GME)
BNA: 106348783 106348790 106348855 106367760 106382501
BOE: 106305965 106322505
RSZ: 108809026 108836738 108855455
THJ: 104818631 104821677
CPAP: 110809701
CIT: 102614415
TCC: 18600196
LJA: Lj0g3v0283729.1(Lj0g3v0283729.1) Lj0g3v0283729.2(Lj0g3v0283729.2) Lj0g3v0283729.3(Lj0g3v0283729.3) Lj0g3v0283729.4(Lj0g3v0283729.4) Lj0g3v0283729.5(Lj0g3v0283729.5) Lj0g3v0283729.6(Lj0g3v0283729.6) Lj1g3v4979970.1(Lj1g3v4979970.1)
ADU: 107492040
AIP: 107645815
FVE: 101304010
PXB: 103954400
CSV: 101222554
CMO: 103495988
MCHA: 111013089
RCU: 8269339
JCU: 105632068
QLO: 115980065
SLY: 100316874(GME2) 100316902(GME1)
LSV: 111916487
CCAV: 112529231
BVG: 104890910
SOE: 110783785
DOSA: Os10t0417600-01(Os10g0417600) Os11t0591100-01(Os11g0591100)
ZMA: 100192102(IDP512) 100280325(gpm480)
DCT: 110110035
PEQ: 110024305
ATR: 18429544
APRO: F751_1084
FCY: FRACYDRAFT_268332(RMLB2_UXS2_1)
TPS: THAPSDRAFT_41548(GALE3)
GUR: Gura_1677
PPD: Ppro_3571
DPI: BN4_12059
BARH: WN72_29130
RPE: RPE_3503
MEA: Mex_1p4519(gme)
MDI: METDI5125(gme)
MEX: Mext_4131
MCH: Mchl_4499
MPO: Mpop_4613
MNO: Mnod_5604
META: Y590_20590
RVA: Rvan_0027
TSV: DSM104635_00202(gerKI)
MGRY: MSR1_39200(chmD)
MAGQ: MGMAQ_2298
SHY: SHJG_0631
SRW: TUE45_01255(chmD)
PSIM: KR76_22870
AMI: Amir_3678
STI: Sthe_3442
TTR: Tter_1172
SNG: SNE_A01440(gME-2)
MIN: Minf_2227(wcaG)
MKC: kam1_2033
MEAP: MTHMO_1586
PIR: VN12_07765(chmD)
AMUC: Pan181_47390(chmD)
PND: Pla175_49290(chmD)
VBL: L21SP4_02283(gerKI)
ACA: ACP_0749
SUS: Acid_7544
SRU: SRU_0618
SRM: SRM_00247(wcaG) SRM_00716(wcaG)
SLI: Slin_4358
FSN: GS03_00615(chmD)
FBA: FIC_01935
CPRV: CYPRO_2424
HWA: HQ_3510A
 » show all
Reference
1  [PMID:443816]
  Authors
Hebda PA, Behrman EJ, Barber GA.
  Title
The guanosine 5'-diphosphate D-mannose: guanosine 5'-diphosphate L-galactose epimerase of Chlorella pyrenoidosa. Chemical synthesis of guanosine 5'-diphosphate L-galactose and further studies of the enzyme and the reaction it catalyzes.
  Journal
Arch Biochem Biophys 194:496-502 (1979)
DOI:10.1016/0003-9861(79)90644-1
Reference
2  [PMID:7098948]
  Authors
Barber GA, Hebda PA.
  Title
GDP-D-mannose: GDP-L-galactose epimerase from Chlorella pyrenoidosa.
  Journal
Methods Enzymol 83:522-5 (1982)
DOI:10.1016/0076-6879(82)83046-2
Reference
3  [PMID:11752432]
  Authors
Wolucka BA, Persiau G, Van Doorsselaere J, Davey MW, Demol H, Vandekerckhove J, Van Montagu M, Zabeau M, Boerjan W
  Title
Partial purification and identification of GDP-mannose 3",5"-epimerase of Arabidopsis thaliana, a key enzyme of the plant vitamin C pathway.
  Journal
Proc Natl Acad Sci U S A 98:14843-8 (2001)
DOI:10.1073/pnas.011578198
Reference
4  [PMID:16366586]
  Authors
Major LL, Wolucka BA, Naismith JH
  Title
Structure and function of GDP-mannose-3',5'-epimerase: an enzyme which performs three chemical reactions at the same active site.
  Journal
J Am Chem Soc 127:18309-20 (2005)
DOI:10.1021/ja056490i
Reference
5  [PMID:16413588]
  Authors
Watanabe K, Suzuki K, Kitamura S
  Title
Characterization of a GDP-D-mannose 3'',5''-epimerase from rice.
  Journal
Phytochemistry 67:338-46 (2006)
DOI:10.1016/j.phytochem.2005.12.003
Other DBs
ExplorEnz - The Enzyme Database: 5.1.3.18
IUBMB Enzyme Nomenclature: 5.1.3.18
ExPASy - ENZYME nomenclature database: 5.1.3.18
BRENDA, the Enzyme Database: 5.1.3.18
CAS: 72162-82-4

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