C-1027 : Cluster information

Compound

Entry name	C-1027
Synonym	Lidamycin
Moiety description	A: enediyne core B: (S)-3-chloro-4,5-dihydroxy-beta-phenylalanine moiety
PKS Type	A: TypeI iterative B: NRPS
Starter Unit	A: acetyl-CoA
Chain Length	A: 8
Sugar Unit	4-deoxy-4-dimehtylamino-5,5-dimethyl-D-ribopyranose
Classification	Enediyne
Activity	Antibiotic Antitumor
Composition	C₄₃H₄₂ClN₃O₁₃

Original source

Organism	Streptomyces globisporus
Strain	C-1027
Contig	AY048670

PKS/NRPS Module

A	C1027_00520 sgcE	1	acetyl-CoA malonyl-CoA
B	C1027_00310 sgcC5	1
	C1027_00340 sgcC1	1	L-alpha-tyrosine
	C1027_00320 sgcC2	1

KS	2..411

AT	619..847

ACP	929..1021

KR	1203..1383

DH	1453..1608

PPT	1710..1923

C	13..317

A	396..808

PCP	13..79

Reference

Genes for production of the enediyne antitumor antibiotic C-1027 in Streptomyces globisporus are clustered with the cagA gene that encodes the C-1027 apoprotein.: Liu W, Shen B
[PMID: 10639366]Antimicrob Agents Chemother. 44 (2000) 382-92
Biosynthesis of the enediyne antitumor antibiotic C-1027.: Liu W, Christenson SD, Standage S, Shen B
[PMID: 12183628]Science. 297 (2002) 1170-3
A genomics-guided approach for discovering and expressing cryptic metabolic pathways.: Zazopoulos E, Huang K, Staffa A, Liu W, Bachmann BO, Nonaka K, Ahlert J, Thorson JS, Shen B, Farnet CM
[PMID: 12536216]Nat Biotechnol. 21 (2003) 187-90
A novel 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis.: Christenson SD, Liu W, Toney MD, Shen B
[PMID: 12785829]J Am Chem Soc. 125 (2003) 6062-3
Rapid PCR amplification of minimal enediyne polyketide synthase cassettes leads to a predictive familial classification model.: Liu W, Ahlert J, Gao Q, Wendt-Pienkowski E, Shen B, Thorson JS
[PMID: 14528002]Proc Natl Acad Sci U S A. 100 (2003) 11959-63
Kinetic analysis of the 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis.: Christenson SD, Wu W, Spies MA, Shen B, Toney MD
[PMID: 14580219]Biochemistry. 42 (2003) 12708-18
Biochemical characterization of the SgcA1 alpha-D-glucopyranosyl-1-phosphate thymidylyltransferase from the enediyne antitumor antibiotic C-1027 biosynthetic pathway and overexpression of sgcA1 in Streptomyces globisporus to improve C-1027 production.: Murrell JM, Liu W, Shen B
[PMID: 14987060]J Nat Prod. 67 (2004) 206-13
Biosynthesis of the beta-amino acid moiety of the enediyne antitumor antibiotic C-1027 featuring beta-amino acyl-S-carrier protein intermediates.: Van Lanen SG, Dorrestein PC, Christenson SD, Liu W, Ju J, Kelleher NL, Shen B
[PMID: 16104723]J Am Chem Soc. 127 (2005) 11594-5
Substrate specificity of the adenylation enzyme SgcC1 involved in the biosynthesis of the enediyne antitumor antibiotic C-1027.: Van Lanen SG, Lin S, Dorrestein PC, Kelleher NL, Shen B
[PMID: 16887797]J Biol Chem. 281 (2006) 29633-40
The structure of L-tyrosine 2,3-aminomutase from the C-1027 enediyne antitumor antibiotic biosynthetic pathway.: Christianson CV, Montavon TJ, Van Lanen SG, Shen B, Bruner SD
[PMID: 17516659]Biochemistry. 46 (2007) 7205-14
Regiospecific chlorination of (S)-beta-tyrosyl-S-carrier protein catalyzed by SgcC3 in the biosynthesis of the enediyne antitumor antibiotic C-1027.: Lin S, Van Lanen SG, Shen B
[PMID: 17887753]J Am Chem Soc. 129 (2007) 12432-8
Design and characterization of mechanism-based inhibitors for the tyrosine aminomutase SgTAM.: Montavon TJ, Christianson CV, Festin GM, Shen B, Bruner SD
[PMID: 18078753]Bioorg Med Chem Lett. 18 (2008) 3099-102
Biosynthesis of the enediyne antitumor antibiotic C-1027 involves a new branching point in chorismate metabolism.: Van Lanen SG, Lin S, Shen B
[PMID: 18182490]Proc Natl Acad Sci U S A. 105 (2008) 494-9
A phosphopantetheinylating polyketide synthase producing a linear polyene to initiate enediyne antitumor antibiotic biosynthesis.: Zhang J, Van Lanen SG, Ju J, Liu W, Dorrestein PC, Li W, Kelleher NL, Shen B
[PMID: 18223152]Proc Natl Acad Sci U S A. 105 (2008) 1460-5
Characterization of the two-component, FAD-dependent monooxygenase SgcC that requires carrier protein-tethered substrates for the biosynthesis of the enediyne antitumor antibiotic C-1027.: Lin S, Van Lanen SG, Shen B
[PMID: 18426211]J Am Chem Soc. 130 (2008) 6616-23
Role of sgcR3 in positive regulation of enediyne antibiotic C-1027 production of Streptomyces globisporus C-1027.: Wang L, Hu Y, Zhang Y, Wang S, Cui Z, Bao Y, Jiang W, Hong B
[PMID: 19159491]BMC Microbiol. 9 (2009) 14
A free-standing condensation enzyme catalyzing ester bond formation in C-1027 biosynthesis.: Lin S, Van Lanen SG, Shen B
[PMID: 19246381]Proc Natl Acad Sci U S A. 106 (2009) 4183-8
Characterization of SgcE6, the flavin reductase component supporting FAD-dependent halogenation and hydroxylation in the biosynthesis of the enediyne antitumor antibiotic C-1027.: Van Lanen SG, Lin S, Horsman GP, Shen B
[PMID: 19817865]FEMS Microbiol Lett. 300 (2009) 237-41
Characterization of the SgcF epoxide hydrolase supporting an (R)-vicinal diol intermediate for enediyne antitumor antibiotic C-1027 biosynthesis.: Lin S, Horsman GP, Chen Y, Li W, Shen B
[PMID: 19856960]J Am Chem Soc. 131 (2009) 16410-7
Manipulation of pathway regulation in Streptomyces globisporus for overproduction of the enediyne antitumor antibiotic C-1027.: Chen Y, Yin M, Horsman GP, Huang S, Shen B
[PMID: 20551990]J Antibiot (Tokyo). 63 (2010) 482-5
Probing the active site of MIO-dependent aminomutases, key catalysts in the biosynthesis of beta-amino acids incorporated in secondary metabolites.: Cooke HA, Bruner SD
[PMID: 20577998]Biopolymers. 93 (2010) 802-10
Improvement of the enediyne antitumor antibiotic C-1027 production by manipulating its biosynthetic pathway regulation in Streptomyces globisporus.: Chen Y, Yin M, Horsman GP, Shen B
[PMID: 21250756]J Nat Prod. 74 (2011) 420-4
Specificity of the ester bond forming condensation enzyme SgcC5 in C-1027 biosynthesis.: Lin S, Huang T, Horsman GP, Huang SX, Guo X, Shen B
[PMID: 22519717]Org Lett. 14 (2012) 2300-3
Draft genome sequence of Streptomyces globisporus C-1027, which produces an antitumor antibiotic consisting of a nine-membered enediyne with a chromoprotein.: Wang L, Wang S, He Q, Yu T, Li Q, Hong B
[PMID: 22815456]J Bacteriol. 194 (2012) 4144
Predictive model for epoxide hydrolase-generated stereochemistry in the biosynthesis of nine-membered enediyne antitumor antibiotics.: Horsman GP, Lechner A, Ohnishi Y, Moore BS, Shen B
[PMID: 23844627]Biochemistry. 52 (2013) 5217-24
Enediyne polyketide synthases stereoselectively reduce the beta-ketoacyl intermediates to beta-D-hydroxyacyl intermediates in enediyne core biosynthesis.: Ge HM, Huang T, Rudolf JD, Lohman JR, Huang SX, Guo X, Shen B
[PMID: 25019332]Org Lett. 16 (2014) 3958-61
Complete genome sequence of Streptomyces globisporus C-1027, the producer of an enediyne antibiotic lidamycin.: Li X, Lei X, Zhang C, Jiang Z, Shi Y, Wang S, Wang L, Hong B
[PMID: 26853480]J Biotechnol. 222 (2016) 9-10
Crystal structure of SgcJ, an NTF2-like superfamily protein involved in biosynthesis of the nine-membered enediyne antitumor antibiotic C-1027.: Huang T, Chang CY, Lohman JR, Rudolf JD, Kim Y, Chang C, Yang D, Ma M, Yan X, Crnovcic I, Bigelow L, Clancy S, Bingman CA, Yennamalli RM, Babnigg G, Joachimiak A, Phillips GN, Shen B
[PMID: 27406907]J Antibiot (Tokyo). 69 (2016) 731-740