clavulanic acid (Q415709)

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Β-lactam molecule used as β-lactamase inhibitor to overcome antibiotic resistance in bacteria
  • (2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • Clavulanic Acid
  • Clavulansaeure
  • Acidum clavulanicum
  • Acide clavulanique
  • MM 14151
  • Acido clavulanico
  • Antibiotic mm 14151
  • BRL-14151
  • ácido clavulánico
  • Clavulansäure
  • clavulonic acid
  • Clavulanate
  • acide clavulanique
  • Antibiotic MM 14151
  • Clavulanic acid
edit
Language Label Description Also known as
English
clavulanic acid
Β-lactam molecule used as β-lactamase inhibitor to overcome antibiotic resistance in bacteria
  • (2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • Clavulanic Acid
  • Clavulansaeure
  • Acidum clavulanicum
  • Acide clavulanique
  • MM 14151
  • Acido clavulanico
  • Antibiotic mm 14151
  • BRL-14151
  • ácido clavulánico
  • Clavulansäure
  • clavulonic acid
  • Clavulanate
  • acide clavulanique
  • Antibiotic MM 14151
  • Clavulanic acid

Statements

subclass of
alkaloid
0 references
chemical structure
Clavulanic acid.svg
512 × 360; 5 KB
0 references
mass
199.048 dalton
1 reference
stated in
PubChem
PubChem CID
5280980
language of work or name
English
title
CLAVULANIC ACID (English)
retrieved
19 October 2016
chemical formula
C₈H₉NO₅
1 reference
stated in
PubChem
PubChem CID
5280980
language of work or name
English
title
CLAVULANIC ACID (English)
retrieved
19 November 2016
canonical SMILES
C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
1 reference
stated in
PubChem
PubChem CID
5280980
language of work or name
English
title
CLAVULANIC ACID (English)
retrieved
19 November 2016
isomeric SMILES
C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
1 reference
stated in
PubChem
PubChem CID
5280980
language of work or name
English
title
CLAVULANIC ACID (English)
retrieved
19 November 2016
found in taxon
Streptomyces clavuligerus
69 references
stated in
The origin of the β-lactam carbons of clavulanic acid
stated in
Evidence that arginine is a later metabolic intermediate than ornithine in the biosynthesis of clavulanic acid by Streptomyces clavuligerus
stated in
Evidence that the immediate biosynthetic precursor of clavulanic acid is its N-aldehyde analogue
stated in
Biosynthesis of clavulanic acid: origin of the C3 unit
stated in
Biosynthesis of clavulanic acid: origin of the C5 unit
stated in
The stereochemical fate of (2RS,5R)- and (2RS,5S)-[5-3H]ornithine in clavulanic acid biosynthesis
stated in
Clavulanic acid biosynthesis: the stereochemical course of β-lactam formation from chiral glycerol
stated in
The role of molecular oxygen in clavulanic acid biosynthesis: evidence for a bacterial oxidative deamination
stated in
Cloning, sequencing and disruption of a gene from Streptomyces clavuligerus involved in clavulanic acid biosynthesis.
stated in
A novel finding that Streptomyces clavuligerus can produce the antibiotic clavulanic acid using olive oil as a sole carbon source.
stated in
Induction of holomycin production and complex metabolic changes by the argR mutation in Streptomyces clavuligerus NP1.
stated in
Data set of in silico simulation for the production of clavulanic acid and cephamycin C by Streptomyces clavuligerus using a genome scale metabolic model
stated in
Two sets of paralogous genes encode the enzymes involved in the early stages of clavulanic acid and clavam metabolite biosynthesis in Streptomyces clavuligerus
stated in
A putative antimicrobial peptide from Hymenoptera in the megaplasmid pSCL4 of ATCC 27064 reveals a singular case of horizontal gene transfer with potential applications
stated in
An improved HPLC-DAD method for clavulanic acid quantification in fermentation broths of Streptomyces clavuligerus.
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Coordination of glycerol utilization and clavulanic acid biosynthesis to improve clavulanic acid production in Streptomyces clavuligerus
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Homologous expression of lysA encoding diaminopimelic acid (DAP) decarboxylase reveals increased antibiotic production in Streptomyces clavuligerus
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The claR gene of Streptomyces clavuligerus, encoding a LysR-type regulatory protein controlling clavulanic acid biosynthesis, is linked to the clavulanate-9-aldehyde reductase (car) gene.
stated in
Mutants of Streptomyces clavuligerus with disruptions in different genes for clavulanic acid biosynthesis produce large amounts of holomycin: possible cross-regulation of two unrelated secondary metabolic pathways
stated in
A pathway-specific transcriptional activator regulates late steps of clavulanic acid biosynthesis in Streptomyces clavuligerus
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Clavulanic acid production estimation based on color and structural features of Streptomyces clavuligerus bacteria using self-organizing map and genetic algorithm.
stated in
Role of the cmcH-ccaR intergenic region and ccaR overexpression in cephamycin C biosynthesis in Streptomyces clavuligerus
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Genome-wide gene expression changes in an industrial clavulanic acid overproduction strain of Streptomyces clavuligerus
stated in
Different proteins bind to the butyrolactone receptor protein ARE sequence located upstream of the regulatory ccaR gene of Streptomyces clavuligerus
stated in
Proteome-wide alterations in an industrial clavulanic acid producing strain of Streptomyces clavuligerus
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Functional analysis of the gene encoding the clavaminate synthase 2 isoenzyme involved in clavulanic acid biosynthesis in Streptomyces clavuligerus
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Improvement of clavulanic acid production in Streptomyces clavuligerus by genetic manipulation of structural biosynthesis genes
stated in
A statistical approach using L(25) orthogonal array method to study fermentative production of clavulanic acid by Streptomyces clavuligerus MTCC 1142.
stated in
Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus
stated in
5S clavam biosynthetic genes are located in both the clavam and paralog gene clusters in Streptomyces clavuligerus.
stated in
Clavulanic acid production by the MMS 150 mutant obtained from wild type Streptomyces clavuligerus ATCC 27064.
stated in
In vivo functional analysis of a class A β-lactamase-related protein essential for clavulanic acid biosynthesis in Streptomyces clavuligerus
stated in
Effect of water activity on production of beta-lactam antibiotics by Streptomyces clavuligerus in submerged culture
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5S clavam biosynthesis is controlled by an atypical two-component regulatory system in Streptomyces clavuligerus
stated in
Improved production of clavulanic acid by reverse engineering and overexpression of the regulatory genes in an industrial Streptomyces clavuligerus strain
stated in
Characterization of DNA-binding sequences for CcaR in the cephamycin-clavulanic acid supercluster of Streptomyces clavuligerus
stated in
Streptomyces clavuligerus has a second copy of the proclavaminate amidinohydrolase gene
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Role of σ-factor (orf21) in clavulanic acid production in Streptomyces clavuligerus NRRL3585.
stated in
Proteomics analysis of global regulatory cascades involved in clavulanic acid production and morphological development in Streptomyces clavuligerus
stated in
Enhanced biosynthesis of clavulanic acid in Streptomyces clavuligerus due to oxidative challenge by redox-cycling agents
stated in
High concentrations of clavulanic acid but not of its degradation products decrease glycerol consumption and oxygen uptake rates in cultures of Streptomyces clavuligerus
stated in
Characterization of the Metabolic Response of Streptomyces clavuligerus to Shear Stress in Stirred Tanks and Single-Use 2D Rocking Motion Bioreactors for Clavulanic Acid Production
stated in
Morphological differentiation and clavulanic acid formation are affected in a Streptomyces clavuligerus adpA-deleted mutant
stated in
A comparison of the clavam biosynthetic gene clusters in Streptomyces antibioticus Tü1718 and Streptomyces clavuligerus
stated in
Streptomyces clavuligerus shows a strong association between TCA cycle intermediate accumulation and clavulanic acid biosynthesis.
stated in
Activation of Secondary Metabolite Gene Clusters in by the PimM Regulator of
stated in
Draft genome sequence of Streptomyces clavuligerus NRRL 3585, a producer of diverse secondary metabolites.
stated in
Expression of ccaR, encoding the positive activator of cephamycin C and clavulanic acid production in Streptomyces clavuligerus, is dependent on bldG.
stated in
Dissociation of cephamycin C and clavulanic acid biosynthesis by 1,3-diaminopropane in Streptomyces clavuligerus.
stated in
Production of clavulanic acid and cephamycin C by Streptomyces clavuligerus in palm-oil medium
stated in
An approach to strain improvement and enhanced production of clavulanic acid in Streptomyces clavuligerus
stated in
Improvement for the production of clavulanic acid by mutant Streptomyces clavuligerus
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Screening of medium constituents for clavulanic acid production by Streptomyces clavuligerus.
stated in
A quantitative approach to characterizing cell lysis caused by mechanical agitation of Streptomyces clavuligerus.
stated in
Expansion of the clavulanic acid gene cluster: identification and in vivo functional analysis of three new genes required for biosynthesis of clavulanic acid by Streptomyces clavuligerus
stated in
Morphology and clavulanic acid production of Streptomyces clavuligerus: Effect of stirrer speed in batch fermentations
stated in
Transcriptional Studies on a Streptomyces clavuligerus oppA2 Deletion Mutant: N-Acetylglycyl-Clavaminic Acid Is an Intermediate of Clavulanic Acid Biosynthesis
stated in
Complete Genome Sequence of Streptomyces clavuligerus F613-1, an Industrial Producer of Clavulanic Acid
stated in
The CagRS Two-Component System Regulates Clavulanic Acid Metabolism via Multiple Pathways in F613-1
stated in
An rplKDelta29-PALG-32 mutation leads to reduced expression of the regulatory genes ccaR and claR and very low transcription of the ceaS2 gene for clavulanic acid biosynthesis in Streptomyces clavuligerus
stated in
Shear conditions in clavulanic acid production by Streptomyces clavuligerus in stirred tank and airlift bioreactors.
stated in
Clavulanic acid production by Streptomyces clavuligerus: biogenesis, regulation and strain improvement
stated in
The positive activator of cephamycin C and clavulanic acid production in Streptomyces clavuligerus is mistranslated in a bldA mutant
stated in
Identification of the gene cluster for the dithiolopyrrolone antibiotic holomycin in Streptomyces clavuligerus
stated in
Streptomyces clavuligerus relA-null mutants overproduce clavulanic acid and cephamycin C: negative regulation of secondary metabolism by (p)ppGpp
stated in
Application of Acid and Cold Stresses to Enhance the Production of Clavulanic Acid by Streptomyces clavuligerus
stated in
Clavulanic acid: a beta-lactamase-inhiting beta-lactam from Streptomyces clavuligerus
stated in
Five additional genes are involved in clavulanic acid biosynthesis in Streptomyces clavuligerus.
stated in
Enzymes catalyzing the early steps of clavulanic acid biosynthesis are encoded by two sets of paralogous genes in Streptomyces clavuligerus
has part(s)
carbon
0 references
Commons category
Clavulanic acid
0 references

Identifiers

PubChem CID
5280980
1 reference
stated in
PubChem
PubChem CID
5280980
language of work or name
English
title
CLAVULANIC ACID (English)
retrieved
19 November 2016
Reaxys registry number
787059
1 reference
stated in
ChEBI
ChEBI ID
48947
language of work or name
English
title
clavulanic acid (English)
retrieved
19 October 2016
ChEMBL ID
CHEMBL777
1 reference
stated in
ChEMBL
ChEMBL ID
CHEMBL777
language of work or name
English
title
CLAVULANIC ACID (English)
retrieved
19 November 2016
ECHA Substance Infocard ID
100.055.500
1 reference
stated in
ECHA Substance Infocard database
ECHA Substance Infocard ID
100.055.500
retrieved
27 December 2018
title
Clavulanic acid (English)
quotation
CAS no.: 58001-44-8 (English)
KNApSAcK ID
C00018091
1 reference
stated in
ChEBI
ChEBI ID
48947
language of work or name
English
title
clavulanic acid (English)
retrieved
19 October 2016
KEGG ID
D07711
1 reference
stated in
ChEBI
ChEBI ID
48947
language of work or name
English
title
clavulanic acid (English)
retrieved
19 October 2016
PDB ligand ID
J01
0 references
CAB ID
60862
1 reference
stated in
CAB Thesaurus
retrieved
6 April 2020
 
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