KEGG   ORTHOLOGY: K00559Help
Entry
K00559                      KO                                     

Name
SMT1, ERG6
Definition
sterol 24-C-methyltransferase [EC:2.1.1.41]
Pathway
ko00100  Steroid biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko01130  Biosynthesis of antibiotics
Module
M00102  Ergocalciferol biosynthesis
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00100 Steroid biosynthesis
    K00559  SMT1, ERG6; sterol 24-C-methyltransferase
Enzymes [BR:ko01000]
 2. Transferases
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.41  sterol 24-C-methyltransferase
     K00559  SMT1, ERG6; sterol 24-C-methyltransferase
BRITE hierarchy
Other DBs
RN: R04427 R07481
COG: COG0500
GO: 0003838
Genes
BFO: BRAFLDRAFT_70257
NAI: NECAME_03546
AQU: 100639491
ATH: AT5G13710(SMT1)
ALY: ARALYDRAFT_909323
CRB: 17882375
CSAT: 104705624 104735382 104769590
EUS: EUTSA_v10014014mg
BRP: 103850891 103856028
BNA: 106371823 106384356 106392091 106431054 106440921
CPAP: 110809321
CIT: 102628258
GRA: 105790583
GAB: 108470188
VRA: 106760797
VAR: 108332339
VUN: 114165537
CAM: 101497864
LJA: Lj0g3v0067279.1(Lj0g3v0067279.1) Lj3g3v0825030.1(Lj3g3v0825030.1) Lj3g3v0825030.2(Lj3g3v0825030.2)
FVE: 101293342
RCN: 112181939
PPER: 18785581
PMUM: 103330640
PAVI: 110765835
JCU: 105628730
SIND: 105169293
CCAV: 112522572
BVG: 104907757
SOE: 110778345
NNU: 104597375
DOSA: Os03t0807600-00(Os03g0807600) Os07t0206700-01(Os07g0206700) Os11t0296900-00(Os11g0296900)
ATS: 109734415(LOC109734415) 109756778(LOC109756778)
AOF: 109833715
SMO: SELMODRAFT_449609(SMT1-2) SELMODRAFT_449613(SMT1-1)
MIS: MICPUN_93596(SMT1)
SCE: YML008C(ERG6)
ERC: Ecym_4063
KMX: KLMA_30671(ERG6)
NCS: NCAS_0H02570(NCAS0H02570)
NDI: NDAI_0C01050(NDAI0C01050)
TPF: TPHA_0D02350(TPHA0D02350)
TBL: TBLA_0D01630(TBLA0D01630)
TDL: TDEL_0A03930(TDEL0A03930)
KAF: KAFR_0C05410(KAFR0C05410)
CAL: CAALFM_C302150CA(ERG6)
CDU: CD36_82130(ERG6)
SLB: AWJ20_2170(ERG6)
NCR: NCU02502 NCU03006(erg-4)
NTE: NEUTE1DRAFT150553(NEUTE1DRAFT_150553) NEUTE1DRAFT73978(NEUTE1DRAFT_73978)
MAW: MAC_08238
MBE: MBM_07594
ANG: ANI_1_256124(An14g01590) ANI_1_752184(An04g04210)
PTE: PTT_11273
SPO: SPBC16E9.05(erg6)
CNE: CNB03100
CNB: CNBB2600
LBC: LACBIDRAFT_184995(erg6)
ABP: AGABI1DRAFT115299(AGABI1DRAFT_115299)
ABV: AGABI2DRAFT194260(AGABI2DRAFT_194260)
MGL: MGL_2877
MRT: MRET_3473
DDI: DDB_G0288907(smt1)
DFA: DFA_09943(smt1)
SMIN: v1.2.010320.t1(symbB.v1.2.010320.t1) v1.2.020967.t1(symbB.v1.2.020967.t1) v1.2.040208.t1(symbB.v1.2.040208.t1)
SPAR: SPRG_05001
TMC: LMI_2904
NDK: I601_4050(rebM_4)
 » show all
TaxonomyKoalaUniProt
Reference
  Authors
Jayasimha P, Nes WD
  Title
Photoaffinity labeling and mutational analysis of 24-C-sterol methyltransferase defines the AdoMet binding site.
  Journal
Lipids 43:681-93 (2008)
DOI:10.1007/s11745-008-3198-x
  Sequence
[sce:YML008C]
Reference
  Authors
Ganapathy K, Kanagasabai R, Nguyen TT, Nes WD
  Title
Purification, characterization and inhibition of sterol C24-methyltransferase from Candida albicans.
  Journal
Arch Biochem Biophys 505:194-201 (2011)
DOI:10.1016/j.abb.2010.10.008
  Sequence
Reference
  Authors
Diener AC, Li H, Zhou W, Whoriskey WJ, Nes WD, Fink GR
  Title
Sterol methyltransferase 1 controls the level of cholesterol in plants.
  Journal
Plant Cell 12:853-70 (2000)
DOI:10.1105/tpc.12.6.853
  Sequence
[ath:AT5G13710]

KEGG   ENZYME: 2.1.1.41Help
Entry
EC 2.1.1.41                 Enzyme                                 

Name
sterol 24-C-methyltransferase;
Delta24-methyltransferase;
Delta24-sterol methyltransferase;
zymosterol-24-methyltransferase;
S-adenosyl-4-methionine:sterol Delta24-methyltransferase;
SMT1;
24-sterol C-methyltransferase;
S-adenosyl-L-methionine:Delta24(23)-sterol methyltransferase;
phytosterol methyltransferase
Class
Transferases;
Transferring one-carbon groups;
Methyltransferases
BRITE hierarchy
Sysname
S-adenosyl-L-methionine:zymosterol 24-C-methyltransferase
Reaction(IUBMB)
S-adenosyl-L-methionine + 5alpha-cholesta-8,24-dien-3beta-ol = S-adenosyl-L-homocysteine + 24-methylene-5alpha-cholest-8-en-3beta-ol [RN:R04427]
Reaction(KEGG)
R04427;
(other) R07481
Show
Substrate
S-adenosyl-L-methionine [CPD:C00019];
5alpha-cholesta-8,24-dien-3beta-ol [CPD:C05437]
Product
S-adenosyl-L-homocysteine [CPD:C00021];
24-methylene-5alpha-cholest-8-en-3beta-ol [CPD:C04525]
Comment
Requires glutathione. Acts on a range of sterols with a 24(25)-double bond in the sidechain. While zymosterol is the preferred substrate it also acts on desmosterol, 5alpha-cholesta-7,24-dien-3beta-ol, 5alpha-cholesta-5,7,24-trien-3beta-ol, 4alpha-methylzymosterol and others. S-Adenosyl-L-methionine attacks the Si-face of the 24(25) double bond and the C-24 hydrogen is transferred to C-25 on the Re face of the double bond.
History
EC 2.1.1.41 created 1972, modified 2001
Pathway
ec00100  Steroid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
ec01130  Biosynthesis of antibiotics
Orthology
K00559  sterol 24-C-methyltransferase
Genes
BFO: BRAFLDRAFT_70257
NAI: NECAME_03546
AQU: 100639491
ATH: AT5G13710(SMT1)
ALY: ARALYDRAFT_909323
CRB: 17882375
CSAT: 104705624 104735382 104769590
EUS: EUTSA_v10014014mg
BRP: 103850891 103856028
BNA: 106371823 106384356 106392091 106431054 106440921
CPAP: 110809321
CIT: 102628258
GRA: 105790583
GAB: 108470188
VRA: 106760797
VAR: 108332339
VUN: 114165537
CAM: 101497864
LJA: Lj0g3v0067279.1(Lj0g3v0067279.1) Lj3g3v0825030.1(Lj3g3v0825030.1) Lj3g3v0825030.2(Lj3g3v0825030.2)
FVE: 101293342
RCN: 112181939
PPER: 18785581
PMUM: 103330640
PAVI: 110765835
JCU: 105628730
SIND: 105169293
CCAV: 112522572
BVG: 104907757
SOE: 110778345
NNU: 104597375
DOSA: Os03t0807600-00(Os03g0807600) Os07t0206700-01(Os07g0206700) Os11t0296900-00(Os11g0296900)
ATS: 109734415(LOC109734415) 109756778(LOC109756778)
AOF: 109833715
SMO: SELMODRAFT_449609(SMT1-2) SELMODRAFT_449613(SMT1-1)
MIS: MICPUN_93596(SMT1)
SCE: YML008C(ERG6)
ERC: Ecym_4063
KMX: KLMA_30671(ERG6)
NCS: NCAS_0H02570(NCAS0H02570)
NDI: NDAI_0C01050(NDAI0C01050)
TPF: TPHA_0D02350(TPHA0D02350)
TBL: TBLA_0D01630(TBLA0D01630)
TDL: TDEL_0A03930(TDEL0A03930)
KAF: KAFR_0C05410(KAFR0C05410)
CAL: CAALFM_C302150CA(ERG6)
CDU: CD36_82130(ERG6)
SLB: AWJ20_2170(ERG6)
NCR: NCU02502 NCU03006(erg-4)
NTE: NEUTE1DRAFT150553(NEUTE1DRAFT_150553) NEUTE1DRAFT73978(NEUTE1DRAFT_73978)
MAW: MAC_08238
MBE: MBM_07594
ANG: ANI_1_256124(An14g01590) ANI_1_752184(An04g04210)
PTE: PTT_11273
SPO: SPBC16E9.05(erg6)
CNE: CNB03100
CNB: CNBB2600
LBC: LACBIDRAFT_184995(erg6)
ABP: AGABI1DRAFT115299(AGABI1DRAFT_115299)
ABV: AGABI2DRAFT194260(AGABI2DRAFT_194260)
MGL: MGL_2877
MRT: MRET_3473
DDI: DDB_G0288907(smt1)
DFA: DFA_09943(smt1)
SMIN: v1.2.010320.t1(symbB.v1.2.010320.t1) v1.2.020967.t1(symbB.v1.2.020967.t1) v1.2.040208.t1(symbB.v1.2.040208.t1)
SPAR: SPRG_05001
TMC: LMI_2904
NDK: I601_4050(rebM_4)
 » show all
Taxonomy
Reference
1  [PMID:5354959]
  Authors
Moore JT, Gaylor JL.
  Title
Isolation and purification of an S-adenosylmethionine: delta 24-sterol methyltransferase from yeast.
  Journal
J Biol Chem 244:6334-40 (1969)
Reference
2  [PMID:8597586]
  Authors
Venkatramesh M, Guo DA, Jia Z, Nes WD.
  Title
Mechanism and structural requirements for transformation of substrates by the (S)-adenosyl-L-methionine:delta 24(25)-sterol methyl transferase from Saccharomyces cerevisiae.
  Journal
Biochim Biophys Acta 1299:313-24 (1996)
DOI:10.1016/0005-2760(95)00218-9
Reference
3
  Authors
Tong, Y., McCourt, B.S., Guo, D., Mangla, A.T., Zhou, W.X., Jenkins, M.D., Zhou, W., Lopez, M. and Nes, W.D.
  Title
, Stereochemical features of C-methylation on the path to Delta24(28)-methylene and Delta24(28)-ethylidene sterols: studies on the recombinant phytosterol methyl transferase from Arabidopsis thaliana.
  Journal
Tetrahedron Lett 38:6115-6118 (1997)
Reference
4  [PMID:9746350]
  Authors
Bouvier-Nave P, Husselstein T, Benveniste P.
  Title
Two families of sterol methyltransferases are involved in the first and the second methylation steps of plant sterol biosynthesis.
  Journal
Eur J Biochem 256:88-96 (1998)
DOI:10.1046/j.1432-1327.1998.2560088.x
  Sequence
[osa:4342690]
Reference
5  [PMID:9606964]
  Authors
Nes WD, McCourt BS, Zhou WX, Ma J, Marshall JA, Peek LA, Brennan M.
  Title
Overexpression, purification, and stereochemical studies of the recombinant (S)-adenosyl-L-methionine: delta 24(25)- to delta 24(28)-sterol methyl transferase enzyme from Saccharomyces cerevisiae.
  Journal
Arch Biochem Biophys 353:297-311 (1998)
DOI:10.1006/abbi.1998.0665
Other DBs
ExplorEnz - The Enzyme Database: 2.1.1.41
IUBMB Enzyme Nomenclature: 2.1.1.41
ExPASy - ENZYME nomenclature database: 2.1.1.41
BRENDA, the Enzyme Database: 2.1.1.41
CAS: 37257-07-1

KEGG   REACTION: R04427Help
Entry
R04427                      Reaction                               

Name
S-Adenosyl-L-methionine:zymosterol C-methyltransferase
Definition
S-Adenosyl-L-methionine + Zymosterol <=> S-Adenosyl-L-homocysteine + Fecosterol
Equation
Reaction class
RC00003  C00019_C00021
RC01154  C04525_C05437
Enzyme
Pathway
rn00100  Steroid biosynthesis
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00102  Ergocalciferol biosynthesis
Orthology
K00559  sterol 24-C-methyltransferase [EC:2.1.1.41]
Other DBs
RHEA: 21131

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