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A6671

Sigma-Aldrich

Actinonin

≥98% (TLC), powder, leucine aminopeptidase inhibitor

Synonyme(s) :

3-[[1-[(2-(Hydroxymethyl)-1-pyrrolidinyl)carbonyl]-2-methylpropyl]carbamoyl]octanohydroxamic acid

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About This Item

Formule empirique (notation de Hill):
C19H35N3O5
Numéro CAS:
13434-13-4
Poids moléculaire :
385.50
Numéro Beilstein :
1555250
Numéro MDL:
MFCD00080257
Code UNSPSC :
12352200
ID de substance PubChem :
24278232
Nomenclature NACRES :
NA.77

product name

Actinonin,

Source biologique

synthetic (organic)

Pureté

≥98% (TLC)

Forme

powder

Solubilité

ethanol: 50 mg/mL, clear, colorless

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

enzyme | inhibits

Température de stockage

−20°C

Chaîne SMILES 

CCCCCC(CC(=O)NO)C(=O)NC(C(C)C)C(=O)N1CCCC1CO

InChI

1S/C19H35N3O5/c1-4-5-6-8-14(11-16(24)21-27)18(25)20-17(13(2)3)19(26)22-10-7-9-15(22)12-23/h13-15,17,23,27H,4-12H2,1-3H3,(H,20,25)(H,21,24)

Clé InChI

XJLATMLVMSFZBN-UHFFFAOYSA-N

Informations sur le gène

human ... ANPEP(290) , DPP4(1803) , ECE1(1889) , LAP3(51056)

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Description générale

Chemical structure: peptide

Application

Actinonin has been used as a control to inhibit meprin-β activity in C57BL/6 mice. It has also been used to study the high-affinity interaction of EcPDF with actinonin by 15N NMR spectroscopy and isothermal titration.

Actions biochimiques/physiologiques

Actinonin has inhibitory action against peptide deformylase (PDF). It is effective against Gram-positive and fastidious Gram-negative microorganisms.
Actinonin is an inhibitor of leucine aminopeptidase. Actinonin has also been used to improve antibacterial activity and antiobesity therapeutics.

Caractéristiques et avantages

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Ectodomain shedding of CD99 within highly conserved regions is mediated by the metalloprotease meprin $\beta$ and promotes transendothelial cell migration
Bedau T, et al.
Faseb Journal, 31(3), 1226-1237 (2016)
Actinonin, a naturally occurring antibacterial agent, is a potent deformylase inhibitor
Chen DZ, et al.
Biochemistry, 39(6), 1256-1262 (2000)
Diana Mader et al.
Microbes and infection, 12(5), 415-419 (2010-02-17)
The biosynthesis of proteins with N-terminal formylated methionine residues and subsequent protein deformylation are unique and invariant bacterial processes. They are exploited by the capacity of the human innate immune system to sense formylated peptides (FPs) and targeted by the
Sonia Fieulaine et al.
PLoS biology, 9(5), e1001066-e1001066 (2011-06-02)
For several decades, molecular recognition has been considered one of the most fundamental processes in biochemistry. For enzymes, substrate binding is often coupled to conformational changes that alter the local environment of the active site to align the reactive groups
Christopher D Goodman et al.
eLife, 9 (2020-07-18)
The antibiotic actinonin kills malaria parasites (Plasmodium falciparum) by interfering with apicoplast function. Early evidence suggested that actinonin inhibited prokaryote-like post-translational modification in the apicoplast; mimicking its activity against bacteria. However, Amberg Johnson et al. (2017) identified the metalloprotease TgFtsH1
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