KEGG   ENZYME: 1.1.99.31
Entry
EC 1.1.99.31                Enzyme                                 
Name
(S)-mandelate dehydrogenase;
MDH (ambiguous)
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With unknown physiological acceptors
Sysname
(S)-mandelate:acceptor 2-oxidoreductase
Reaction(IUBMB)
(S)-mandelate + acceptor = phenylglyoxylate + reduced acceptor [RN:R03793]
Reaction(KEGG)
R03793 > R07664;
(other) R04160
Substrate
(S)-mandelate [CPD:C01984];
acceptor [CPD:C00028]
Product
phenylglyoxylate [CPD:C02137];
reduced acceptor [CPD:C00030]
Comment
This enzyme is a member of the FMN-dependent alpha-hydroxy-acid oxidase/dehydrogenase family [1]. While all enzymes of this family oxidize the (S)-enantiomer of an alpha-hydroxy acid to an alpha-oxo acid, the ultimate oxidant (oxygen, intramolecular heme or some other acceptor) depends on the particular enzyme. This enzyme transfers the electron pair from FMNH2 to a component of the electron transport chain, most probably ubiquinone [1,2]. It is part of a metabolic pathway in Pseudomonads that allows these organisms to utilize mandelic acid, derivatized from the common soil metabolite amygdalin, as the sole source of carbon and energy [2]. The enzyme has a large active-site pocket and preferentially binds substrates with longer sidechains, e.g. 2-hydroxyoctanoate rather than 2-hydroxybutyrate [1]. It also prefers substrates that, like (S)-mandelate, have beta unsaturation, e.g. (indol-3-yl)glycolate compared with (indol-3-yl)lactate [1]. Esters of mandelate, such as methyl (S)-mandelate, are also substrates [3].
History
EC 1.1.99.31 created 2006
Pathway
ec00627  Aminobenzoate degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K15054  (S)-mandelate dehydrogenase
Genes
KPZKPNIH27_29500
KPKA593_26110
METYMRY16398_22310(lldD)
KINAB182_10085
PDZHHA33_12690
EBCC2U52_20660
SRRSerAS9_2024
SRLSOD_c18970(mdlB)
SRYM621_10465
SPLYQ5A_010505(mdlB_2)
SRSSerAS12_2024
SRASerAS13_2025
SERASer39006_008175
SERQCWC46_08170
RAHRahaq_2166
RACEJHW33_05990
RAQRahaq2_2270
RAAQ7S_10965
ROXBV494_06240
PAOPat9b_5751
TCIA7K98_03450 A7K98_09625
PLUplu1106
PLUMA4R40_05455
XEUXSP_002203
SALYE8E00_11930
SKSFCN78_01675
PMKMDS_0258
PREPCA10_p2200
PPUNPP4_48090
PVRPverR02_09860
PLULFOB45_03525
PSILPMA3_26255
PALLUYA_00945
PSEJHNQ25_00355
PTYJWV26_11420
MBSMRBBS_1292(mdlB)
GPSC427_2349
MIIBTJ40_13130
GAIIMCC3135_15650(mdlB_1) IMCC3135_26020(mdlB_2)
CSACsal_1075
HELHELO_1144
HAKKO116_01583 KO116_03908
HAMHALO3110
HHUAR456_15730
HTTHZS52_06555
KUYFY550_01725
ADIB5T_02858
MMWMmwyl1_1831
MARDIBG28_06545
MARSA8C75_04845
MGEOCFI10_09980
CDIZCEDIAZO_03333(mdlB_2)
RPJN234_37865
REHH16_B1832(mdlB)
CNCCNE_2c17870(mdlB) CNE_BB1p09340(lldA)
REUReut_B3845 Reut_C6258
BOKDM82_843(mdlB)
BOCBG90_87(mdlB)
BCEPAPZ15_29795
BSEMWJ12_27655 WJ12_29785
BGLbglu_1g22680
BGUKS03_3099(mdlB)
BUGBC1001_0562
BGFBC1003_4245 BC1003_5931 BC1003_6041
BGDbgla_1g16560
BGOBM43_2882(mdlB)
BYIBYI23_D002250(mdlB)
BUEBRPE67_DCDS04000(mdlB)
BUQAC233_22965
BGPBGL_1c14480(mdlB)
BPLAbpln_1g14030
BUMAXG89_31730 AXG89_36055
BUIAX768_16445
BURKDM992_18225
BXEBxe_B0136
BXBDR64_5486(mdlB)
BPHBphy_5156 Bphy_6162
BGEBC1002_6152
BPXBUPH_01010 BUPH_02660 BUPH_04446 BUPH_04485
BPYBphyt_6402
BFNOI25_63(mdlB)
PSPWBJG93_28250
PHSC2L64_43710
PCAFDSC91_002503
PMEGFNZ07_00035
PACSFAZ98_17720 FAZ98_22970 FAZ98_33820
PPKU875_17400
PPNODA70_09870
PPNMLV28_21225
PRBX636_17015
PPULRO07_15460
PSPUNA29_21610
PAPISG18_24535
PVEUC34_06685
POXMB84_11135
PFGAB870_17715
PNRAT302_00440
PANDDRB87_06060
PFIBPI93_021585
CABASBC2_42390(mdlB)
BPCBPTD_1648(lldA)
BPETB1917_1591(lldA)
BPEUQ425_18440(lldA)
BBHBN112_2341(lldD)
BBRBB1109(lldD)
BBMBN115_1055(lldD)
BBXBBS798_1077(lldD)
BHOD560_0958(mdlB)
BHMD558_0941(mdlB)
BHZACR54_02380(mdlB_2)
BFZBAU07_00075
BPDZBBN53_10075
BGMCAL15_19635
BOJCBF45_00085
AXONH44784_012131 NH44784_027291
AXNAX27061_0944 AX27061_5576
AXXERS451415_00929(mdlB_1) ERS451415_05599(mdlB_4)
ADTAPT56_25710
AISBUW96_08255
ADYHLG70_24245
PUSCKA81_12955
AKATKWG_21795
AAQUD3M96_18515
AAMMFE795_16070
BOZDBV39_02620 DBV39_02640
PIGEGT29_08500 EGT29_23150 EGT29_27015
PACRFXN63_01975 FXN63_24830
KGYEHF36_00220
PARKLSG25_18645
RHYRD110_17475
PNAPnap_1020
ACKC380_23560
VAPVapar_3912
VPDVAPA_2c12340
VAMC4F17_30270
HYNF9K07_00610 F9K07_00635 F9K07_07145
DIHG7047_08610 G7047_08675
HSEHsero_0244(lldD)
HSZACP92_01205
HRBHrubri_0228(lldD) Hrubri_1083(mdlB)
HFRG5S34_01060
GLCJQN73_20910
DOEDENOEST_2697
APETToN1_43340
AZOazo2470(lldD)
AOAdqs_2614
AZAAZKH_1692(lldD) AZKH_1885
AZIAzCIB_1257
AZDCDA09_08695 CDA09_10570
AZRCJ010_15385
TMZTmz1t_0668
TCLTchl_0094 Tchl_1486
THKCCZ27_17095
TAKTharo_0088 Tharo_3014
MCIMesci_5397
MESRFGU64_10705
MESOBSQ44_18490
MESMeso_3045
RPODE0E05_15920
ARAArad_12221
RTRRTCIAT899_PC05950
RHRCKA34_03290 CKA34_26460
RBQJ2J99_03850
RLNJ0663_14705
NGLRG1141_CH38130 RG1141_PA01780
NGGRG540_CH38780 RG540_PA01870
NEOCYG48_19030
NENNCHU2750_42560(lldA)
OPSA8A54_22875
BJAbll6401(bll6401)
BVZBRAD3257_7347 BRAD3257_7518
BOPAXW83_14795 AXW83_15420
BOSBSY19_3792
BVVBHK69_17470
BOFFQV39_21680 FQV39_24590
AZCAZC_1655
SNOSnov_4068
STARG3545_11180 G3545_16280
MTEADK419_23670
BIDBind_2622
CHELAL346_15935 AL346_22080
RHZRHPLAN_37570
MSCBN69_3477
MPARF7D14_04315
MEYTM49_03690
AALAIGS74_02945
AALMLUX29_01795
BRND1F64_10335
PSINCAK95_00805 CAK95_22435
LABTFIU93_07200(mdlB)
TSVDSM104635_00467(mdlB_1) DSM104635_01763(mdlB_2)
RUAD1823_05125
RUTFIU92_07880(mdlB)
JANJann_1403
RDERD1_3814(lldD)
RLIRLO149_c006310(slcD)
RPONG3256_03845
PGAPGA1_c07690(mdlB)
PGLPGA2_c07470(mdlB)
PGDGal_02722
PPICPhaeoP14_00690(mdlB)
PHQD1820_16920
OATOAN307_c48440
OAROA238_c48420
LEJETW24_02295
LAQUR2C4_00620
CIDP73_2967
CEHCEW89_13885
PABYGa0080574_TMP2102 Ga0080574_TMP346 Ga0080574_TMP3683
SULZC1J03_11945
SULIC1J05_06940
RMMROSMUCSMR3_02357(mdlB)
ROKRAK1035_0826
RIDRIdsm_00829(mdlB_1) RIdsm_01459(mdlB_2)
SAGUCDO87_01815 CDO87_03265
MARUFIU81_11485(mdlB)
ROTFIV09_10455(mdlB1) FIV09_14665(mdlB2)
PDEPden_5045
PPANESD82_06575
TAWEI545_19110
SALOEF888_10865
SEDIEBB79_14305
BOOE2K80_12255
PPRUFDP22_22160
PGVSL003B_3168
GCEKYE46_13935
NPNJI59_21645
NREBES08_01940
SWISwit_4230 Swit_4248
SPHDHY78_17960
RDICMV14_05135
SPYGYGS_C1P2754
SPZRG5C33_10880
ALBAEB_P1898
AAYWYH_00438(mdlB)
CMANA9D14_18035
ERYCP97_05395
SHUMSTHU_48200(lldD)
SVCSTVA_48390(lldD)
STELSTAQ_43510(lldD)
AZLAZL_a11050
ABSAZOBR_p310226(lldD)
ABQABAZ39_28150
ATIAL072_26115
AZTTSH58p_32395
AZMDM194_21165
AOZHUE56_25755 HUE56_26160
SKTIGS68_08990
SMUCJL100_018390
SROEJL101_017090
MAGamb4454
MAGXXM1_0747(lldD) XM1_4569
MAGNWV31_12095
HADHFRZ61_02850(lldA)
APBSAR116_0071
MSAMycsm_01815
MLLB1R94_28780
REQREQ_43160
PSEYGU243_00780
FRAFrancci3_2407
FALFRAAL4104
PAUTPdca_67690
RUBGBA63_02205
OLEK0B96_03035
ARKD6B99_06005
ZSPMQE36_10225
 » show all
Reference
1  [PMID:10231535]
  Authors
Lehoux IE, Mitra B.
  Title
(S)-Mandelate dehydrogenase from Pseudomonas putida: mechanistic studies with alternate substrates and pH and kinetic isotope effects.
  Journal
Biochemistry 38:5836-48 (1999)
DOI:10.1021/bi990024m
Reference
2  [PMID:15311930]
  Authors
Dewanti AR, Xu Y, Mitra B.
  Title
Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity.
  Journal
Biochemistry 43:10692-700 (2004)
DOI:10.1021/bi049005p
Reference
3  [PMID:14967029]
  Authors
Dewanti AR, Xu Y, Mitra B.
  Title
Esters of mandelic acid as substrates for (S)-mandelate dehydrogenase from Pseudomonas putida: implications for the reaction mechanism.
  Journal
Biochemistry 43:1883-90 (2004)
DOI:10.1021/bi036021y
Other DBs
ExplorEnz - The Enzyme Database: 1.1.99.31
IUBMB Enzyme Nomenclature: 1.1.99.31
ExPASy - ENZYME nomenclature database: 1.1.99.31
UM-BBD (Biocatalysis/Biodegradation Database): 1.1.99.31
BRENDA, the Enzyme Database: 1.1.99.31
CAS: 9067-95-2
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