KEGG ENZYME: 4.2.3.7

ENZYME: 4.2.3.7

Entry

EC 4.2.3.7                  Enzyme

Name

pentalenene synthase;
pentalenene synthetase

Class

Lyases;
Carbon-oxygen lyases;
Acting on phosphates

Sysname

(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)

Reaction(IUBMB)

(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate [RN:R02305]

Reaction(KEGG)

R02305

Substrate

(2E,6E)-farnesyl diphosphate [CPD:C00448]

Product

pentalenene [CPD:C01841];
diphosphate [CPD:C00013]

Comment

Isolated from Streptomyces avermitilis. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics. The 9si hydrogen of farnesyl diphosphate undergoes a 1,2-hydride shift where it becomes the 1alpha hydrogen of pentalenene.

History

EC 4.2.3.7 created 1989 as EC 4.6.1.5, transferred 2000 to EC 4.2.3.7

Pathway

ec00909

Sesquiterpenoid and triterpenoid biosynthesis

ec00998

Biosynthesis of various antibiotics

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K12250

pentalenene synthase

Genes

MFB:	MFUL124B02_01475 MFUL124B02_01480

MLAN:

JY572_00075

PTRI:

KDC22_17270

NYU:	D7D52_27555

NVU:	V7968_16060

SMA:	SAVERM_2998(ptlA)

SBH:

SBI_09679

SCI:	B446_29695

SCW:	TU94_27405

SLE:	sle_13160(sle_13160)

SSIA:

A7J05_09240

SRK:	FGW37_27330

SVR:	CP971_04990

SCIN:

CP977_32300

SPLA:

CP981_00105

SHUN:

DWB77_06666(ptlA)

SHAR:

HUT13_06550

SPEU:

CGZ69_00970

SGJ:	IAG43_11500 IAG43_27155

SHK:	J2N69_35805

SMAO:

CAG99_22035

SCAE:

IHE65_36335

SYUN:

MOV08_02850 MOV08_41460

SOV:	QZH56_04205

KBU:	Q4V64_00250

STPB:

QR97_33775

STSD:

HEP87_03355 HEP87_07450

SPIH:

ABXR15_04125

» show all

Reference

1 [PMID:6642060]

Authors

Cane DE.

Title

Cell-free studies of monoterpene and sesquiterpene biosynthesis.

Journal

Biochem Soc Trans 11:510-5 (1983)
DOI:10.1042/bst0110510

Reference

Authors

Cane DE, Tillman AM.

Title

Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate.

Journal

J Am Chem Soc 105:122-124 (1983)

Reference

3 [PMID:8180213]

Authors

Cane DE, Sohng JK, Lamberson CR, Rudnicki SM, Wu Z, Lloyd MD, Oliver JS, Hubbard BR

Title

Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319.

Journal

Biochemistry 33:5846-57 (1994)
DOI:10.1021/bi00185a024

Sequence

[sbh:SBI_09679]

Reference

4 [PMID:1678531]

Authors

Cane DE, Abell C, Harrison PH, Hubbard BR, Kane CT, Lattman R, Oliver JS, Weiner SW

Title

Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions.

Journal

Philos Trans R Soc Lond B Biol Sci 332:123-9 (1991)
DOI:10.1098/rstb.1991.0040

Reference

5 [PMID:9295272]

Authors

Lesburg CA, Zhai G, Cane DE, Christianson DW

Title

Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology.

Journal

Science 277:1820-4 (1997)
DOI:10.1126/science.277.5333.1820

Reference

6 [PMID:22738258]

Authors

Zu L, Xu M, Lodewyk MW, Cane DE, Peters RJ, Tantillo DJ

Title

Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry.

Journal

J Am Chem Soc 134:11369-71 (2012)
DOI:10.1021/ja3043245

Other DBs

ExplorEnz - The Enzyme Database:

4.2.3.7

IUBMB Enzyme Nomenclature:

4.2.3.7

ExPASy - ENZYME nomenclature database:

4.2.3.7

BRENDA, the Enzyme Database:

4.2.3.7

CAS:	90597-46-9

LinkDB

DBGET integrated database retrieval system