Spinosyn : Cluster information
Compound
Entry name | Spinosyn |
---|---|
Synonym | Spinosad (mixture of Spinosyn A and Spinosyn D) |
PKS Type | TypeI modular |
Starter Unit | methylmalonyl-CoA |
Chain Length | 11 |
Sugar Unit | forosamine tri-O-methylrhamnose |
Classification | Macrolide |
Activity | Insecticidal |
Composition | A: C41H65NO10 D: C42H67NO10 E: C40H63NO10 F: C40H63NO10 |
Original source
Organism | Saccharopolyspora spinosa |
---|---|
Strain | NRRL 18538 |
Contig | AY007564 |
PKS/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 |
Reference
- 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
Data download
History
- 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]