KEGG   ORTHOLOGY: K05354
Entry
K05354                      KO                                     
Symbol
TR2
Name
tropinone reductase II [EC:1.1.1.236]
Pathway
map00960  Tropane, piperidine and pyridine alkaloid biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R06734  pseudotropine:NADP+ 3-oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00960 Tropane, piperidine and pyridine alkaloid biosynthesis
    K05354  TR2; tropinone reductase II
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.236  tropinone reductase II
     K05354  TR2; tropinone reductase II
Other DBs
GO: 0050358
Genes
SLY: 101256174
SPEN: 107018368
SOT: 102589607(TRII)
SSTN: 125856831
SDUL: 129871211
CANN: 107872392
LBB: 132615530 132615635 132615940
AG: AAA33282(TR2)
Reference
PMID:8415746
  Authors
Nakajima K, Hashimoto T, Yamada Y
  Title
Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor.
  Journal
Proc Natl Acad Sci U S A 90:9591-5 (1993)
DOI:10.1073/pnas.90.20.9591
  Sequence
[ag:AAA33282]
Reference
PMID:11855731
  Authors
Keiner R, Kaiser H, Nakajima K, Hashimoto T, Drager B
  Title
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).
  Journal
Plant Mol Biol 48:299-308 (2002)
DOI:10.1023/A:1013315110746

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Ontology (1)   
   GO (1)   
Gene (1)   
   OC (1)   
All databases (2)   

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KEGG   ENZYME: 1.1.1.236
Entry
EC 1.1.1.236                Enzyme                                 
Name
tropinone reductase II;
tropinone (psi-tropine-forming) reductase;
pseudotropine forming tropinone reductase;
tropinone reductase (ambiguous);
TR-II
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
pseudotropine:NADP+ 3-oxidoreductase
Reaction(IUBMB)
pseudotropine + NADP+ = tropinone + NADPH + H+ [RN:R06734]
Reaction(KEGG)
R06734
Substrate
pseudotropine [CPD:C02066];
NADP+ [CPD:C00006]
Product
tropinone [CPD:C00783];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
This enzyme along with EC 1.1.1.206, tropine dehydrogenase, represents a branch point in tropane alkaloid metabolism [3]. Tropine (the product of EC 1.1.1.206) is incorporated into hyoscyamine and scopolamine whereas pseudotropine (the product of EC 1.1.1.236) is the first specific metabolite on the pathway to the calystegines [3]. Both enzymes are always found together in any given tropane-alkaloid-producing species, have a common substrate, tropinone, and are strictly stereospecific [2].
History
EC 1.1.1.236 created 1992, modified 2007
Pathway
ec00960  Tropane, piperidine and pyridine alkaloid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K05354  tropinone reductase II
Genes
SLY: 101256174
SPEN: 107018368
SOT: 102589607(TRII)
SSTN: 125856831
SDUL: 129871211
CANN: 107872392
LBB: 132615530 132615635 132615940
Reference
1
  Authors
Drager B, Hashimoto T, Yamada Y.
  Title
Purification and characterization of pseudotropine forming tropinone reductase from Hyoscyamus niger root cultures.
  Journal
Agric Biol Chem 52:2663-2667 (1988)
Reference
2
  Authors
Couladis MM Friesen JB, Landgrebe ME, Leete E.
  Title
Enzymes catalysing the reduction of tropinone to tropine and psi-tropine isolated from the roots of Datura innoxia.
  Journal
Pytochemistry 30:801-805 (1991)
Reference
3  [PMID:8415746]
  Authors
Nakajima K, Hashimoto T, Yamada Y
  Title
Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor.
  Journal
Proc Natl Acad Sci U S A 90:9591-5 (1993)
DOI:10.1073/pnas.90.20.9591
  Sequence
[ag:AAA33282]
Reference
4  [PMID:16426652]
  Authors
Drager B.
  Title
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.
  Journal
Phytochemistry 67:327-37 (2006)
DOI:10.1016/j.phytochem.2005.12.001
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.236
IUBMB Enzyme Nomenclature: 1.1.1.236
ExPASy - ENZYME nomenclature database: 1.1.1.236
BRENDA, the Enzyme Database: 1.1.1.236
CAS: 136111-61-0

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Protein sequence (31)   
   UniProt (16)   
   SWISS-PROT (3)   
   PDBSTR (11)   
   PMD (1)   
DNA sequence (20)   
   GenBank (10)   
   EMBL (10)   
3D Structure (6)   
   PDB (6)   
Protein domain (5)   
   InterPro (4)   
   PROSITE(DOC) (1)   
All databases (62)   

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KEGG   REACTION: R06734
Entry
R06734                      Reaction                               
Name
pseudotropine:NADP+ 3-oxidoreductase
Definition
Tropinone + NADPH + H+ <=> Pseudotropine + NADP+
Equation
C00783 + C00005 + C00080 <=> C02066 + C00006
Comment
pseudotropine forming tropinone reductase
Reaction class
RC00001  C00005_C00006
RC00144  C00783_C02066
Enzyme
1.1.1.236
Pathway
rn00960  Tropane, piperidine and pyridine alkaloid biosynthesis
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.236
     R06734  Tropinone + NADPH + H+ <=> Pseudotropine + NADP+
Orthology
K05354  tropinone reductase II [EC:1.1.1.236]
Other DBs
RHEA: 24247

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Chemical reaction (1)   
   SABIO-RK (1)   
All databases (1)   

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