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Merck

A6671

Actinonin

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

Synonym(s):

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

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About This Item

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

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Product Name

Actinonin,

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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This Item
A1276A6191I0160
Actinonin

Sigma-Aldrich

A6671

Actinonin

Amastatin hydrochloride hydrate ≥97% (HPLC)

Sigma-Aldrich

A1276

Amastatin hydrochloride hydrate

Antipain dihydrochloride from microbial source protease inhibitor

Sigma-Aldrich

A6191

Antipain dihydrochloride from microbial source

Imipenem monohydrate ≥98% (HPLC)

Sigma-Aldrich

I0160

Imipenem monohydrate

assay

≥98% (TLC)

assay

≥97% (HPLC)

assay

-

assay

≥98% (HPLC)

form

powder

form

powder

form

lyophilized powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

ethanol: 50 mg/mL, clear, colorless

solubility

methanol: 1 mM (Stock solution stable for 1 month at −20 °C. Working solution stable for 1 day.)

solubility

H2O: 50 mg/mL, 1-butanol: soluble, 1-propanol: soluble, DMSO: soluble, ethanol: soluble, methanol: soluble

solubility

H2O: >5 mg/mL

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

Streptomyces sp.

biological source

-

General description

Chemical structure: peptide

Application

Actinonin has been used as a control to inhibit meprin-β activity in C57BL/6 mice.[1] It has also been used to study the high-affinity interaction of EcPDF with actinonin by 15N NMR spectroscopy and isothermal titration.[2]

Biochem/physiol Actions

Actinonin has inhibitory action against peptide deformylase (PDF). It is effective against Gram-positive and fastidious Gram-negative microorganisms.[3]
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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000476747
0000476747
0000385028
0000383134
0000376563

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Jennifer Hamner et al.
Scientific reports, 10(1), 6358-6358 (2020-04-15)
Vaginal delivery with obstetrical trauma is a risk factor for pelvic organ prolapse later in life. Loss of fibulin-5 (FBLN5), an elastogenesis-promoting cellular matrix protein, results in prolapse in mice. Here, we evaluated effects of pregnancy, parturition, and obstetrical injury
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
Ligand-induced changes in the structure and dynamics of Escherichia coli peptide deformylase
Amero CD, et al.
Biochemistry, 48(32), 7595-7607 (2009)
Actinonin, a naturally occurring antibacterial agent, is a potent deformylase inhibitor
Chen DZ, et al.
Biochemistry, 39(6), 1256-1262 (2000)
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
View All Related Papers

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