Bz-IEGR-pNA (acetate) Chemical Properties

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

form 

A crystalline solid

Sequence

{Bz-Ile}-Glu-Gly-Arg-{pNA}

InChIKey

ITXQNZUGLZNGBM-SFKTYRLKNA-N

SMILES

C(=O)(O)C.N(C1C=CC(N(=O)=O)=CC=1)C(=O)[C@H](CCCNC(N)=N)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@]([H])([C@@H](C)CC)NC(C1C=CC=CC=1)=O |&1:16,31,40,42,r|

Bz-IEGR-pNA (acetate) Usage And Synthesis

Description

Bz-IEGR-pNA acetate is a colorimetric substrate for Factor Xa. Factor Xa preferentially binds to and cleaves the Ile-Glu-Gly-Arg (IEGR) peptide sequence to release p-nitroanilide (pNA), which can be quantified by colorimetric detection at 405 nm as a measure of Factor Xa activity.

Uses

Bz-IEGR-pNA acetate is a trypsin substrate that can be hydrolyzed by prostate kinase release enzyme-related peptide KLKs[1].

Structure and conformation

The structure of Bz-IEGR-PNA Acetate is complex and contains several functional groups. One end consists of a benzoyl group (Bz), which is somewhat hydrophobic and can influence the molecule's interactions with other substances. The middle portion is a peptide composed of isoleucine (Ile), glutamic acid (Glu), glycine (Gly), and arginine (Arg), linked by peptide bonds.
Isoleucine has a long hydrophobic side chain that enhances the molecule's overall hydrophobicity.
Glutamic acid contains a carboxyl group, making it acidic.
Glycine has the simplest structure and is the smallest amino acid.
Arginine features a guanidinium group in its side chain, giving it strong basicity.
The peptide's amino acid sequence and structure determine its binding affinity to specific enzymes. The other end is attached to p-nitroaniline (PNA), whose nitro group is strongly electron-withdrawing, enabling this moiety to play a unique role in specific reactions. The entire molecule is conjugated with acetate to form Bz-IEGR-PNA Acetate; the acetate moiety may influence the compound's solubility and ionic properties in solution.

References

[1] Guo S, et al. Activation and activity of glycosylated KLKs 3, 4 and 11. Biol Chem. 2018 Sep 25;399(9):1009-1022. DOI:10.1515/hsz-2018-0148

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