KEGG   ORTHOLOGY: K00559
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
Module
M00102  Ergocalciferol biosynthesis, squalene 2,3-epoxide => ergosterol/ergocalciferol
M00917  Phytosterol biosynthesis, squalene 2,3-epoxide => campesterol/sitosterol
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
Other DBs
RN: R04427 R07481
COG: COG0500
GO: 0003838
Genes
BMY: Bm1_45250
NAI: NECAME_03546
AQU: 100639491
ATH: AT5G13710(SMT1)
ALY: 9307650
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: 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)
OBR: 102713236
ATS: 109734415(LOC109734415) 109756778(LOC109756778)
AOF: 109833715
SMO: SELMODRAFT_449609(SMT1-2) SELMODRAFT_449613(SMT1-1)
PPP: 112291818
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)
ANG: ANI_1_1324144(An16g00300) ANI_1_256124(An14g01590) ANI_1_752184(An04g04210)
PTE: PTT_11273
SPO: SPBC16E9.05(erg6)
CNE: CNB03100
CNB: CNBB2600
TASA: A1Q1_06727
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
LPAN: LPMP_352450(LMSMT)
TMC: LMI_2904
NDK: I601_4050(rebM_4)
SUS: Acid_3267
 » show all
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: 2.1.1.41
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
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
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
Orthology
K00559  sterol 24-C-methyltransferase
Genes
BMY: Bm1_45250
NAI: NECAME_03546
AQU: 100639491
ATH: AT5G13710(SMT1)
ALY: 9307650
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: 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)
OBR: 102713236
ATS: 109734415(LOC109734415) 109756778(LOC109756778)
AOF: 109833715
SMO: SELMODRAFT_449609(SMT1-2) SELMODRAFT_449613(SMT1-1)
PPP: 112291818
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)
ANG: ANI_1_1324144(An16g00300) ANI_1_256124(An14g01590) ANI_1_752184(An04g04210)
PTE: PTT_11273
SPO: SPBC16E9.05(erg6)
CNE: CNB03100
CNB: CNBB2600
TASA: A1Q1_06727
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
LPAN: LPMP_352450(LMSMT)
TMC: LMI_2904
NDK: I601_4050(rebM_4)
SUS: Acid_3267
 » show all
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: R04427
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
rn01110  Biosynthesis of secondary metabolites
Module
M00102  Ergocalciferol biosynthesis, squalene 2,3-epoxide => ergosterol/ergocalciferol
Orthology
K00559  sterol 24-C-methyltransferase [EC:2.1.1.41]
Other DBs
RHEA: 21131

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