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Merck
CN

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:
Molecular Weight:
385.50
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Beilstein/REAXYS Number:
1555250
Assay:
≥98% (TLC)
Form:
powder
Quality level:
Technical Service
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Product Name

Actinonin,

biological source

synthetic (organic)

Quality Level

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

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.


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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



Global Trade Item Number

SKUGTIN
A6671-25MG04061833382646
A6671-10MG04061833258477