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Nocardicin A

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Nocardicin A
Names
IUPAC name (2R)-2-Amino-4--2-oxoazetidin-3- yl]carbamoyl]carbonimidoyl]phenoxy]butanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/b26-18+/t16-,17+,19-/m1/s1Key: CTNZOGJNVIFEBA-TWTPMLPMSA-N
  • InChI=1/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/b26-18+/t16-,17+,19-/m1/s1Key: CTNZOGJNVIFEBA-TWTPMLPMBJ
SMILES
  • O=C(O)(c1ccc(O)cc1)N3C(=O)(NC(=O)\C(=N\O)c2ccc(OCC(C(=O)O)N)cc2)C3
Properties
Chemical formula C23H24N4O9
Molar mass 500.46 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Nocardicin A is a monocyclic β-lactam antibiotic included in the monobactam subclass. It is obtained from the fermentation broth of a strain of actinomycetes Nocardia uniformis subsp. tsuyamenensis as a metabolic product catalyzed by the enzyme nocardicin-A epimerase. It is stereochemically and biologically related to penicillin and cephalosporins.

Biosynthesis of Nocardicin A

References

  1. "Nocardicin A". pubchem.ncbi.nlm.nih.gov. Retrieved 12 March 2023.
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
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