close all open/close all
Jump cluster list

Cluster information : Spinosyn


close this sectionCompound

Entry nameSpinosyn
SynonymSpinosad (mixture of Spinosyn A and Spinosyn D)
PKS TypeTypeI modular
Starter Unitmethylmalonyl-CoA
Chain Length11
Sugar Unitforosamine
tri-O-methylrhamnose
ClassificationMacrolide
ActivityInsecticidal
CompositionA: C41H65NO10
D: C42H67NO10
E: C40H63NO10
F: C40H63NO10
Spinosyn

close this sectionOriginal source

Organism
StrainNRRL 18538
Contig
Click on the icon to see Genetic map.

close this sectionPKS/NRPS Module

Spino_00170
spnA
0 methylmalonyl-CoA
1 malonyl-CoA
Spino_00180
spnB
2 malonyl-CoA
Spino_00190
spnC
3 methylmalonyl-CoA
4 malonyl-CoA
Spino_00200
spnD
5 malonyl-CoA
6 malonyl-CoA
7 malonyl-CoA
Spino_00210
spnE
8 methylmalonyl-CoA
9 malonyl-CoA
10 malonyl-CoA
KSQ8..375
AT527..844
ACP907..977
KS997..1366
AT1525..1846
KR2160..2339
ACP2444..2514
KS37..413
AT572..893
DH940..1102
ER1413..1715
KR1725..1903
ACP2001..2071
KS34..410
AT563..881
KR1194..1369
ACP1470..1540
KS1561..1937
AT2099..2420
KR2735..2914
ACP3017..3087
KS38..414
AT576..894
DH942..1104
KR1421..1601
ACP1692..1762
KS1787..2162
AT2320..2642
KR2955..3134
ACP3233..3307
KS3328..3703
AT3862..4181
KR4495..4674
ACP4774..4844
KS34..410
AT563..878
DH928..1093
KR1404..1584
ACP1684..1758
KS1782..2159
AT2320..2638
DH2685..2874
KR3193..3373
ACP3462..3532
KS3559..3934
AT4093..4411
DH4458..4619
KR4933..5113
ACP5217..5287
TE5364..5577

close this sectionReference

Cloning and analysis of the spinosad biosynthetic gene cluster of Saccharopolyspora spinosa.
Waldron C, Matsushima P, Rosteck PR Jr, Broughton MC, Turner J, Madduri K, Crawford KP, Merlo DJ, Baltz RH
[PMID: 11358695]Chem Biol. 8 (2001) 487-99
A cluster of genes for the biosynthesis of spinosyns, novel macrolide insect control agents produced by Saccharopolyspora spinosa.
Waldron C, Madduri K, Crawford K, Merlo DJ, Treadway P, Broughton MC, Baltz RH
[PMID: 11386361]Antonie Van Leeuwenhoek. 78 (2000) 385-90
Rhamnose biosynthesis pathway supplies precursors for primary and secondary metabolism in Saccharopolyspora spinosa.
Madduri K, Waldron C, Merlo DJ
[PMID: 11544225]J Bacteriol. 183 (2001) 5632-8
Engineered biosynthesis of novel spinosyns bearing altered deoxyhexose substituents.
Gaisser S, Martin CJ, Wilkinson B, Sheridan RM, Lill RE, Weston AJ, Ready SJ, Waldron C, Crouse GD, Leadlay PF, Staunton J
[PMID: 12120151]Chem Commun (Camb). (2002) 618-9
Heterologous expression in Saccharopolyspora erythraea of a pentaketide synthase derived from the spinosyn polyketide synthase.
Martin CJ, Timoney MC, Sheridan RM, Kendrew SG, Wilkinson B, Staunton JC, Leadlay PF
[PMID: 14685317]Org Biomol Chem. 1 (2003) 4144-7
Characterization of protein encoded by spnR from the spinosyn gene cluster of Saccharopolyspora spinosa: mechanistic implications for forosamine biosynthesis.
Zhao Z, Hong L, Liu HW
[PMID: 15913355]J Am Chem Soc. 127 (2005) 7692-3
Characterization of SpnQ from the spinosyn biosynthetic pathway of Saccharopolyspora spinosa: mechanistic and evolutionary implications for C-3 deoxygenation in deoxysugar biosynthesis.
Hong L, Zhao Z, Liu HW
[PMID: 17076492]J Am Chem Soc. 128 (2006) 14262-3
The biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of the cross-bridging precursor and identification of the function of SpnJ.
Kim HJ, Pongdee R, Wu Q, Hong L, Liu HW
[PMID: 17985910]J Am Chem Soc. 129 (2007) 14582-4
In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa.
Hong L, Zhao Z, Melancon CE 3rd, Zhang H, Liu HW
[PMID: 18345667]J Am Chem Soc. 130 (2008) 4954-67
SpnH from Saccharopolyspora spinosa encodes a rhamnosyl 4'-O-methyltransferase for biosynthesis of the insecticidal macrolide, spinosyn A.
Huang KX, Zahn J, Han L
[PMID: 18704529]J Ind Microbiol Biotechnol. 35 (2008) 1669-76
Functional characterization and substrate specificity of spinosyn rhamnosyltransferase by in vitro reconstitution of spinosyn biosynthetic enzymes.
Chen YL, Chen YH, Lin YC, Tsai KC, Chiu HT
[PMID: 19126547]J Biol Chem. 284 (2009) 7352-63
Glycosylation engineering of spinosyn analogues containing an L-olivose moiety.
Gaisser S, Carletti I, Schell U, Graupner PR, Sparks TC, Martin CJ, Wilkinson B
[PMID: 19343260]Org Biomol Chem. 7 (2009) 1705-8
The spinosyn family of insecticides: realizing the potential of natural products research.
Kirst HA
[PMID: 20150928]J Antibiot (Tokyo). 63 (2010) 101-11
Biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of permethylated rhamnose and characterization of the functions of SpnH, SpnI, and SpnK.
Kim HJ, White-Phillip JA, Ogasawara Y, Shin N, Isiorho EA, Liu HW
[PMID: 20158237]J Am Chem Soc. 132 (2010) 2901-3
Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A.
Kim HJ, Ruszczycky MW, Choi SH, Liu YN, Liu HW
[PMID: 21544146]Nature. 473 (2011) 109-12
Structural studies of the spinosyn rhamnosyltransferase, SpnG.
Isiorho EA, Liu HW, Keatinge-Clay AT
[PMID: 22283226]Biochemistry. 51 (2012) 1213-22
Divergence of multimodular polyketide synthases revealed by a didomain structure.
Zheng J, Gay DC, Demeler B, White MA, Keatinge-Clay AT
[PMID: 22634636]Nat Chem Biol. 8 (2012) 615-21
Structural studies of the spinosyn forosaminyltransferase, SpnP.
Isiorho EA, Jeon BS, Kim NH, Liu HW, Keatinge-Clay AT
[PMID: 24945604]Biochemistry. 53 (2014) 4292-301
The structure of SpnF, a standalone enzyme that catalyzes [4 + 2] cycloaddition.
Fage CD, Isiorho EA, Liu Y, Wagner DT, Liu HW, Keatinge-Clay AT
[PMID: 25730549]Nat Chem Biol. 11 (2015) 256-8
Natural Diels-Alderases: Elusive and Irresistable.
Klas K, Tsukamoto S, Sherman DH, Williams RM
[PMID: 26495876]J Org Chem. 80 (2015) 11672-85
Dynamically Complex [6+4] and [4+2] Cycloadditions in the Biosynthesis of Spinosyn A.
Patel A, Chen Z, Yang Z, Gutierrez O, Liu HW, Houk KN, Singleton DA
[PMID: 26909570]J Am Chem Soc. 138 (2016) 3631-4
Alteration of Polyketide Stereochemistry from anti to syn by a Ketoreductase Domain Exchange in a Type I Modular Polyketide Synthase Subunit.
Eng CH, Yuzawa S, Wang G, Baidoo EE, Katz L, Keasling JD
[PMID: 26976746]Biochemistry. 55 (2016) 1677-80

close this sectionData download

Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Spinosyn
Genomic nucleotide sequence
81 KB
Nucleotide sequences of the coding regions
78 KB
Translation of the coding sequences
27 KB
List of genes/ORFs
4 KB

 

 
GenBank format
151 KB

close this sectionHistory

  • 2016-12-27[Update]
  • 2016-01-27[Update]
  • 2015-02-12[Update]
  • 2013-01-16[Update]
  • 2012-10-02[Update]
  • 2012-08-03[Update]
  • 2012-03-28[Release]