Fluorophosphonate-nocardicin-G
methyl fluorophosphonate derivative of nocardicin G inhibiting dual-function epimerase/thioesterase domain of polyketide synthase. On MUY and CID the fluor residue is gone
General
Type : Organophosphate,Azetidin
Chemical_Nomenclature : Fluorophosphonate nocardicin G || [(S)-[(3S)-3-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-2-oxoazetidin-1-yl]-(4-hydroxyphenyl)methyl]-methylphosphinic acid
Canonical SMILES : C1(=CC=C(C=C1)[C@H]([P@@](=O)(F)OC)N2C[C@@H](C2=O)NC([C@@H](C3=CC=C(C=C3)O)N)=O)O || CP(=O)(C(C1=CC=C(C=C1)O)N2CC(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)O
InChI : InChI=1S\/C19H21FN3O6P\/c1-29-30(20,28)19(12-4-8-14(25)9-5-12)23-10-15(18(23)27)22-17(26)16(21)11-2-6-13(24)7-3-11\/h2-9,15-16,19,24-25H,10,21H2,1H3,(H,22,26)\/t15-,16+,19-,30-\/m0\/s1 || InChI=1S\/C19H22N3O6P\/c1-29(27,28)19(12-4-8-14(24)9-5-12)22-10-15(18(22)26)21-17(25)16(20)11-2-6-13(23)7-3-11\/h2-9,15-16,19,23-24H,10,20H2,1H3,(H,21,25)(H,27,28)\/t15-,16+,19-\/m0\/s1
InChIKey : OVSLOWSETATXNU-KTZAHZSOSA-N || SAUAKDHLYZXRHJ-FCEWJHQRSA-N
Other name(s) : Fluorophosphonate nocardicin G,MUY
MW : 437.36 || 419.4
Formula : C19H21FN3O6P || C19H22N3O6P
CAS_number :
PubChem : 145946087
UniChem : OVSLOWSETATXNU-KTZAHZSOSA-N || SAUAKDHLYZXRHJ-FCEWJHQRSA-N
IUPHAR :
Wikipedia :
Target
Families : Fluorophosphonate-nocardicin-G ligand of proteins in family: Thioesterase
Stucture : 6OJD A high-resolution crystal structure of covalent complex of NocB thioesterase domain with fluorophosphonate nocardicin G analog
Protein : 9noca-q5j1q6
References (2)
| Title : Late-Stage Conversion of Diphenylphosphonate to Fluorophosphonate Probes for the Investigation of Serine Hydrolases - d'Andrea_2019_Cell.Chem.Biol_26_878 |
| Author(s) : d'Andrea FB , Townsend CA |
| Ref : Cell Chemical Biology , 26 :878 , 2019 |
| Abstract : d'Andrea_2019_Cell.Chem.Biol_26_878 |
| ESTHER : d'Andrea_2019_Cell.Chem.Biol_26_878 |
| PubMedSearch : d'Andrea_2019_Cell.Chem.Biol_26_878 |
| PubMedID: 30982751 |
| Gene_locus related to this paper: 9noca-q5j1q6 |
| Title : Structure of a bound peptide phosphonate reveals the mechanism of nocardicin bifunctional thioesterase epimerase-hydrolase half-reactions - Patel_2019_Nat.Commun_10_3868 |
| Author(s) : Patel KD , d'Andrea FB , Gaudelli NM , Buller AR , Townsend CA , Gulick AM |
| Ref : Nat Commun , 10 :3868 , 2019 |
| Abstract : Patel_2019_Nat.Commun_10_3868 |
| ESTHER : Patel_2019_Nat.Commun_10_3868 |
| PubMedSearch : Patel_2019_Nat.Commun_10_3868 |
| PubMedID: 31455765 |
| Gene_locus related to this paper: 9noca-q5j1q6 |