Off-loading Dieckmann cyclase, NcmC, that installs the tetramate head group in nocamycin, a hybrid polyketide/nonribosomalpeptide natural product. A conserved thioesterase-like scaffold has been adapted to perform a new chemical reaction: heterocyclization. The catalytic triad for the cyclization reaction consists of Cys89, Asp116, and His254 in 9pseu-NcmC. Dieckmann cyclase (TrdC, SlgL, LipX2, KirHI,and FacH) last step which generate actinomycete-derived tetramic acid and pyridone natural products in the biosynthetic pathways for Tirandamycin, Streptolydigin, alpha-Lipomycin, Kirromycin, and Factumycin
Interpro : No interpro
PIRSF : No PIRSF
Pdoc : No Pdoc
Pfam : No Pfam
Prints : No Print
EC Number : No EC Number
Peptide in | Fasta |
Nucleotide in | Fasta |
Alignment with Multalin | Text only |
Seed alignment with MAFFT | No colour / coloured with Mview |
Alignment with MAFFT | No colour / coloured with Mview |
Dendrogram | The dnd file |
Structure | Name | Proteins |
---|---|---|
6E6T | Dieckmann cyclase from Saccharothrix syringae, NcmC, bound to cerulenin | 9pseu-NcmC |
6E6U | Variant C89S of Dieckmann cyclase, NcmC | 9pseu-NcmC |
6E6Y | Dieckmann cyclase from Saccharothrix syringae, NcmC | 9pseu-NcmC |
Gene_locus | Name | Species |
---|---|---|
9actn-a0a0c1x845 | Streptomyces sp. AcH 505. Uncharacterized protein | Streptomyces sp. AcH 505 |
9actn-a0a0c5fv25 | Streptomyces cyaneogriseus subsp. noncyanogenus. Uncharacterized protein | Streptomyces cyaneogriseus subsp. noncyanogenus |
9actn-a0a0f4k5z7 | Streptomyces sp. NRRL B-1568. Uncharacterized protein | Streptomyces sp. NRRL B-1568 |
9actn-a0a0f4k9s3 | Streptomyces sp. NRRL B-1568. Uncharacterized protein | Streptomyces sp. NRRL B-1568 |
9actn-a0a0k9xby7 | Streptomyces caatingaensis. Uncharacterized protein | Streptomyces caatingaensis |
9actn-a0a0m8v9z7 | Streptomyces sp. MMG1121. Uncharacterized protein | Streptomyces sp. MMG1121 |
9actn-a0a0n1npe0 | Actinobacteria bacterium OK074. Uncharacterized protein | Actinobacteria bacterium OK074 |
9actn-a0a0n6w4z6 | Streptomyces sp. CCM_MD2014. Uncharacterized protein | Streptomyces sp. CCM_MD2014 |
9actn-a0a0n6zgx9 | Streptomyces sp. CCM_MD2014. Uncharacterized protein | Streptomyces sp. CCM_MD2014 |
9actn-a0a0p4rci1 | Streptomyces lydicamycinicus. Uncharacterized protein | Streptomyces lydicamycinicus |
9actn-a0a0q8zxb5 | Streptomyces sp. Root264. Uncharacterized protein | Streptomyces sp. Root264 |
9actn-a0a0t6lq39 | Streptomyces vitaminophilus. Uncharacterized protein | Streptomyces vitaminophilus |
9actn-a0a101n5d4 | Streptomyces cellostaticus. Uncharacterized protein | Streptomyces cellostaticus |
9actn-a0a1c4rpf7 | Streptomyces sp. Termitarium-T10T-6. Uncharacterized protein | Streptomyces sp. Termitarium-T10T-6 |
9actn-a0a1c5gc05 | Micromonospora echinofusca. Uncharacterized protein | Micromonospora echinofusca |
9actn-a0a1c5gdx1 | Micromonospora echinofusca\; Micromonospora peucetia. Uncharacterized protein | Micromonospora echinofusca |
9actn-a0a1c6uku8 | Micromonospora peucetia. Uncharacterized protein | Micromonospora peucetia |
9actn-a0a1c6v190 | Micromonospora eburnea. Uncharacterized protein | Micromonospora eburnea |
9actn-a0a1d2i704 | Streptomyces sp. AVP053U2. Uncharacterized protein | Streptomyces sp. AVP053U2 |
9actn-a0a1h5kkh3 | Streptomyces sp. 2314.4. Uncharacterized protein | Streptomyces sp. 2314.4 |
9actn-a0a1h9jgw2 | Streptomyces radiopugnans. Uncharacterized protein | Streptomyces radiopugnans |
9actn-a0a1h9xtc3 | Streptomyces sp. yr375. Uncharacterized protein | Streptomyces sp. yr375 |
9actn-a0a1h9xtl3 | Streptomyces sp. yr375. Uncharacterized protein | Streptomyces sp. yr375 |
9actn-a0a1q4zi93 | Streptomyces sp. TSRI0281. Uncharacterized protein | Streptomyces sp. TSRI0281 |
9actn-a0a1q5d7w2 | Streptomyces sp. CB01249. Uncharacterized protein | Streptomyces sp. CB01249 |
9actn-a0a1q5fgx4 | Streptomyces sp. CB00316. Uncharacterized protein | Streptomyces sp. CB00316 |
9actn-a0a1q5le62 | Streptomyces sp. CB03234. Uncharacterized protein | Streptomyces sp. CB03234 |
9actn-a0a1q5mn15 | Streptomyces sp. CB00455. Uncharacterized protein | Streptomyces sp. CB00455 |
9actn-a0a1v3zz37 | Streptomyces tsukubensis. Uncharacterized protein | Streptomyces tsukubensis |
9actn-a0a1z2kz73 | Streptomyces albireticuli. Uncharacterized protein | Streptomyces albireticuli |
9actn-a0a209cpb4 | Streptomyces sp. CS227. Uncharacterized protein | Streptomyces sp. CS227 |
9actn-a0a243s3g0 | Streptomyces swartbergensis. Uncharacterized protein | Streptomyces swartbergensis |
9actn-a0a248ypn6 | Plantactinospora sp. KBS50. Uncharacterized protein | Plantactinospora sp. KBS50 |
9actn-a0a248yq89 | Plantactinospora sp. KBS50. Uncharacterized protein | Plantactinospora sp. KBS50 |
9actn-a0a285qt70 | Streptomyces sp. 1331.2. Uncharacterized protein | Streptomyces sp. 1331.2 |
9actn-a0a2a2d3k0 | Streptomyces albireticuli. Uncharacterized protein | Streptomyces albireticuli |
9actn-a0a2g7f626 | Streptomyces sp. 70. Uncharacterized protein | Streptomyces sp. 70 |
9actn-a0a2i0sd64 | Streptomyces populi. Uncharacterized protein | Streptomyces populi |
9actn-a0a2m9ifq0 | Streptomyces sp. CB01373. Uncharacterized protein | Streptomyces sp. CB01373 |
9actn-a0a2n3uyx7 | Streptomyces sp. GP55. Uncharacterized protein | Streptomyces sp. GP55 |
9actn-a0a2n3zbk3 | Micromonospora sp. CNZ309. Uncharacterized protein | Micromonospora sp. CNZ309 |
9actn-a0a2p4uhl0 | Actinomadura sp. RB29. Uncharacterized protein | Actinomadura sp. RB29 |
9actn-a0a2v2pzg2 | Streptomyces sp. ZEA17I. Uncharacterized protein | Streptomyces sp. ZEA17I |
9actn-a0a327vse8 | Streptomyces sp. PsTaAH-137. Uncharacterized protein | Streptomyces sp. PsTaAH-137 |
9actn-a0a344uav3 | Streptomyces globosus. Uncharacterized protein | Streptomyces globosus |
9actn-a0a3a9zgz5 | Micromonospora endolithica. Uncharacterized protein | Micromonospora endolithica |
9actn-a0a3n1d0i7 | Actinocorallia herbida. Uncharacterized protein | Actinocorallia herbida |
9actn-a0a438lz38 | Nonomuraea polychroma. Uncharacterized protein | Nonomuraea polychroma |
9actn-a0a4r3c594 | Streptomyces sp. BK308. Uncharacterized protein | Streptomyces sp. BK308 |
9actn-a0a4r4n079 | Nonomuraea longispora. Uncharacterized protein | Nonomuraea longispora |
9actn-a0a4r5c3h5 | Actinomadura sp. H3C3. Uncharacterized protein | Actinomadura sp. H3C3 |
9actn-a0a514jvg4 | Streptomyces asterosporus\; Streptomyces calvus. Uncharacterized protein Cal14 | Streptomyces asterosporus |
9actn-a0a5r9lrh5 | Streptomyces sp. So13.3. Uncharacterized protein | Streptomyces sp. So13.3 |
9actn-a0a5r9mb21 | Streptomyces sp. So13.3. Uncharacterized protein | Streptomyces sp. So13.3 |
9actn-d1glt3 | Streptomyces lydicus. Uncharacterized protein slgL | Streptomyces lydicus |
9actn-d9xle7 | Streptomyces griseoflavus Tu4000. Uncharacterized protein | Streptomyces griseoflavus Tu4000 |
9actn-f1di35 | Streptomyces sp. TrdC\; TamC. Dieckmann_Cyclase in biosynthetic gene cluster of the bacterial RNA polymerase inhibitor tirandamycin | Streptomyces sp. SCSIO 1666 |
9actn-q9fb38 | Streptomyces verticillus\; Streptomyces mobaraensis. Dieckmann_Cyclase in gene cluster for the antitumor drug bleomycin synthesis | Streptomyces verticillus |
9actn-r4lg32 | Actinoplanes sp. N902-109. Uncharacterized protein | Actinoplanes sp. N902-109 |
9actn-s3bz19 | Streptomyces sp. HPH0547. Uncharacterized protein | Streptomyces sp. HPH0547 |
9pseu-NcmC | ![]() |
Saccharothrix syringae |
9pseu-a0a1b1zjb9 | Pseudonocardia sp. HH130630-07. Uncharacterized protein | Pseudonocardia sp. HH130630-07 |
9pseu-a0a1d8byt1 | Actinoalloteichus hymeniacidonis. Uncharacterized protein | Actinoalloteichus hymeniacidonis |
9pseu-a0a1h2h606 | Amycolatopsis keratiniphila. Uncharacterized protein | Amycolatopsis keratiniphila |
9pseu-a0a1h9wug6 | Lentzea flaviverrucosa. Uncharacterized protein | Lentzea flaviverrucosa |
9pseu-a0a1q4xtq2 | Saccharothrix sp. CB00851. Uncharacterized protein | Saccharothrix sp. CB00851 |
9pseu-a0a1v2q4p3 | Actinosynnema sp. ALI-1.44. Uncharacterized protein | Actinosynnema sp. ALI-1.44 |
9pseu-a0a1v2qtm6 | Saccharothrix sp. ALI-22-I. Uncharacterized protein | Saccharothrix sp. ALI-22-I |
9pseu-a0a290z691 | Actinosynnema pretiosum. Uncharacterized protein | Actinosynnema pretiosum |
9pseu-a0a2n8mh05 | Amycolatopsis sp. BJA-103. Uncharacterized protein | Amycolatopsis sp. BJA-103 |
9pseu-a0a495w3m4 | Saccharothrix australiensis. Uncharacterized protein | Saccharothrix australiensis |
9pseu-a0a495x9w9 | Saccharothrix variisporea. Uncharacterized protein | Saccharothrix variisporea |
9pseu-a0a4r2juc1 | Actinocrispum wychmicini. Uncharacterized protein | Actinocrispum wychmicini |
9pseu-a0a4r7uw25 | Actinophytocola oryzae. Uncharacterized protein | Actinophytocola oryzae |
9pseu-a0a4r7vjx1 | Actinophytocola oryzae. Uncharacterized protein | Actinophytocola oryzae |
9pseu-a0a4v3cy71 | Labedaea rhizosphaerae. Uncharacterized protein | Labedaea rhizosphaerae |
9pseu-a0a4v3ft28 | Actinophytocola oryzae. Uncharacterized protein | Actinophytocola oryzae |
9pseu-a0a542djd2 | Amycolatopsis cihanbeyliensis. Uncharacterized protein | Amycolatopsis cihanbeyliensis |
9pseu-a0a5q0h698 | Saccharothrix syringae. Uncharacterized protein | Saccharothrix syringae |
9pseu-r1hz43 | Amycolatopsis vancoresmycina\; Amycolatopsis sp. var15 Uncharacterized protein | Amycolatopsis vancoresmycina DSM 44592 |
kitau-q30cs4 | Kitasatospora aureofaciens (Streptomyces aureofaciens). LipX2 Dieckmann_Cyclase in biosynthetic gene cluster for the polyenoyltetramic acid alpha-lipomycin | Kitasatospora aureofaciens |
kitsk-e4nik2 | Kitasatospora setae (Streptomyces setae). Uncharacterized protein | Kitasatospora setae |
strc3-s5vff6 | Streptomyces collinus. kirHI Dieckmann_Cyclase in gene cluster of kirromycin synthesis | Streptomyces collinus |
streu-a0a2n8nw41 | Streptomyces eurocidicus (Streptoverticillium eurocidicus). Uncharacterized protein | Streptomyces eurocidicus |
strne-a0a445ni11 | Streptomyces netropsis (Streptoverticillium netropsis). Uncharacterized protein | Streptomyces netropsis |
strpt-a0a1y2njq2 | Streptomyces platensis\; Streptomyces lydicamycinicus. Uncharacterized protein | Streptomyces platensis |
strrg-k7qrj3 | Streptomyces rugosporus. PyrG2. Dieckmann_Cyclase in biosynthetic gene cluster of pyrroindomycin or Quartromicin | Streptomyces rugosporus |
strrn-a0a0a0nf48 | Streptomyces rapamycinicus\; Streptomyces hygroscopicus. Uncharacterized protein D3C57_121920 | Streptomyces rapamycinicus |
strto-a0a081xit3 | Streptomyces toyocaensis. Uncharacterized protein | Streptomyces toyocaensis |
Gene_locus_frgt | Name | Species |
---|---|---|
9actn-a0a0c2asz4 | Streptomyces sp. AcH 505. Uncharacterized protein | Streptomyces sp. AcH 505 |
9actn-a0a1c4tci8 | Streptomyces sp. DvalAA-43. Uncharacterized protein | Streptomyces sp. DvalAA-43 |
9actn-a0a2w2mxp0 | Streptomyces sp. NTH33. Uncharacterized protein | Streptomyces sp. NTH33 |
9actn-a0a365gym5 | Actinomadura sp. LHW63021. Uncharacterized protein | Actinomadura sp. LHW63021 |
9actn-a0a505dql0 | Streptomyces sporangiiformans. Uncharacterized protein | Streptomyces sporangiiformans |
9actn-d9wms8 | Streptomyces himastatinicus ATCC 53653. AB hydrolase-1 domain-containing protein | Streptomyces himastatinicus ATCC 53653 |
9actn-v6lcv4 | Streptomycetaceae bacterium MP113-05. Uncharacterized protein | Streptomycetaceae bacterium MP113-05 |
Substrate | Chemical Nomenclature | Proteins |
---|---|---|
Cerulenin | (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide | 9pseu-NcmC |
Cerulenin-hemiaminal | (1R,4R,5S)-4-hydroxy-4-[(3E,6E)-octa-3,6-dienyl]-6-oxa-3-azabicyclo[3.1.0]hexan-2-one | 9pseu-NcmC |
N-acetoacetyl-glycyl-SNAC | S-(2-acetamidoethyl)2-(3-oxobutanamido)ethanethioate | 9pseu-NcmC |
Inhibitor | Chemical Nomenclature | Proteins |
---|---|---|
6E6T-HVV | (4S,5R)-4,5-Dihydroxy-5-[(3E,6E)-octa-3,6-dienyl]pyrrolidin-2-one | 9pseu-NcmC |
Title : Structural Basis for Enzymatic Off-Loading of Hybrid Polyketides by Dieckmann Condensation - Cogan_2020_ACS.Chem.Biol_15_2783 |
Author(s) : Cogan DP , Ly J , Nair SK |
Ref : ACS Chemical Biology , 15 :2783 , 2020 |
Abstract : |
PubMedSearch : Cogan_2020_ACS.Chem.Biol_15_2783 |
PubMedID: 33017142 |
Gene_locus related to this paper: 9pseu-NcmC |
Title : Discovery of a new family of Dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis - Gui_2015_Org.Lett_17_628 |
Author(s) : Gui C , Li Q , Mo X , Qin X , Ma J , Ju J |
Ref : Org Lett , 17 :628 , 2015 |
Abstract : |
PubMedSearch : Gui_2015_Org.Lett_17_628 |
PubMedID: 25621700 |