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A6671

Sigma-Aldrich

Actinonin

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Synonym(s):
3-[[1-[(2-(Hydroxymethyl)-1-pyrrolidinyl)carbonyl]-2-methylpropyl]carbamoyl]octanohydroxamic acid
Empirical Formula (Hill Notation):
C19H35N3O5
CAS Number:
13434-13-4
Molecular Weight:
385.50
Beilstein:
1555250
MDL number:
MFCD00080257
UNSPSC Code:
12352200
PubChem Substance ID:
24278232
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

ethanol: 50 mg/mL, clear, colorless

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

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)

InChI key

XJLATMLVMSFZBN-UHFFFAOYSA-N

Gene Information

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

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General description

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.

Biochem/physiol Actions

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.

Features and Benefits

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Ligand-induced changes in the structure and dynamics of Escherichia coli peptide deformylase
Amero CD, et al.
Biochemistry, 48(32), 7595-7607 (2009)
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)
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