Benzoyl-L-citrulline methyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Benzoyl-L-citrulline methyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
L-Amino Acids
Catalog number
BAT-007906
CAS number
14325-36-1
Molecular Formula
C14H19N3O4
Molecular Weight
293.32
Benzoyl-L-citrulline methyl ester
IUPAC Name
methyl (2S)-2-benzamido-5-(carbamoylamino)pentanoate
Synonyms
Bz-L-Cit-OMe; (S)-2-Bz-amino-5-ureidopentanoic acid methyl ester; Bz-L-Orn(carbamoyl)-OMe; Benzoyl-L-citrulline methyl ester; (S)-Methyl 2-benzamido-5-ureidopentanoate; Methyl N5-(aminocarbonyl)-N2-benzoyl-L-ornithine; Bzo-Cit-OMe; N-alpha-Benzoyl-L-citrulline methyl ester; L-Ornithine,n5-(aminocarbonyl)-n2-benzoyl-,methyl ester; N-(5-{[Hydroxy(imino)methyl]amino}-1-methoxy-1-oxopentan-2-yl)benzenecarboximidic acid; Bz L Cit OMe; Bzo Cit OM
Appearance
White powder
Purity
≥ 98% (TLC)
Density
1.210 g/cm3
Melting Point
149-158 °C
Boiling Point
533 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H19N3O4/c1-21-13(19)11(8-5-9-16-14(15)20)17-12(18)10-6-3-2-4-7-10/h2-4,6-7,11H,5,8-9H2,1H3,(H,17,18)(H3,15,16,20)/t11-/m0/s1
InChI Key
ARLRYYLMUJSMGC-NSHDSACASA-N
Canonical SMILES
COC(=O)C(CCCNC(=O)N)NC(=O)C1=CC=CC=C1

Benzoyl-L-citrulline methyl ester is an organic compound derived from citrulline, which is an α-amino acid playing a critical role in the urea cycle and nitric oxide production, and the benzoyl group, a functional group characterized by a benzaldehyde removed of one hydrogen atom. The synthesis of this ester involves the modification of citrulline with a benzoyl group, rendering it a potential agent for varied applications in physiological and biochemical fields due to its structural properties which allow it to partake in metabolic processes involving nitrogen balance and signaling pathways.

One of the primary applications of Benzoyl-L-citrulline methyl ester is in biochemical research concerning nitric oxide synthesis. Citrulline itself is a product of nitric oxide synthase reactions and is pivotal in nitric oxide production, a crucial signaling molecule in cardiovascular and immune systems. The use of Benzoyl-L-citrulline methyl ester can thus facilitate studies in pharmacological modulation of nitric oxide pathways, potentially aiding in the development of therapies for hypertension and immune response management.

Another application entails its utility in the biosynthesis analysis concerning the urea cycle, where citrulline is an essential intermediate. Benzoyl-L-citrulline methyl ester can be employed to track or visualize the conversion processes within the cycle, especially under experimental conditions in metabolic disorders research where urea production and ammonia detoxification need to be studied and potentially corrected through biochemical interventions.

Furthermore, Benzoyl-L-citrulline methyl ester finds applications in nutritional science, particularly in examining its efficacy as a supplement that could boost arginine levels in the body due to its derivative relationship. Arginine, reconstructible from citrulline, is a precursor to creatine, thus its study is crucial in research pertinent to muscle metabolism, athletic performance, and recovery solutions, marking the ester as a compound of interest in dietary supplements development.

Lastly, Benzoyl-L-citrulline methyl ester holds promise in clinical diagnostics where citrulline levels could serve as biomarkers for intestinal functioning and health. Research-oriented use of this compound, due to its benzoyl group facilitating easier detection methods, might enhance our understanding of gut health and related pathologies, potentially aiding in non-invasive diagnostic tool development for gastrointestinal disorders.

1. Dependence of the catalytic activity of papain on the ionization of two acidic groups
S D Lewis, F A Johnson, A K Ohno, J A Shafer J Biol Chem. 1978 Jul 25;253(14):5080-6.
The pH dependence of kcat/Km for the papain-catalyzed hydrolysis of ethyl hippurate, N-alpha-benzoyl-L-citrulline methyl ester, and the p-nitroanilide, amide, and ethyl ester derivatives of N-alpha-benzoyl-L-arginine was determined below pH 6.4. The value of kcat/Km was observed to be modulated by two acid ionizations rather than a single ionization as previously believed. For the five substrates studied, the average pK values for the two ionizations are 3.78 +/- 0.2 and 3.95 +/- 0.1 at T/2 0.3, 25 degrees C. The observation that similar pK values were obtained with different substrates was taken as evidence that the kinetically determined pK values are close in value to true macroscopic ionization constants for ionization of groups on the free enzyme.
3. [Structure of the active center of subtilisin 72]
N F Kazanskaia, O A Kost Biokhimiia. 1982 May;47(5):834-41.
The inhibition by N-benzoyl-L-arginine of subtilisin-catalyzed hydrolysis of various substrates was investigated. Study of combined hydrolysis of these substrates revealed the existence of two productive binding sites in the subtilisin 72 molecule. The type of substrate adsorption depends on the nature of the acyl moiety of the molecule and on the nature of the split-off group. The N-acetyl-L-tyrosine ethyl ester and N-benzoyl-L-citrulline methyl ester are bound at the same adsorption site (A), while N-cinnamoyl imidazole and N-acetyl-L-valine methyl ester are found at another adsorption site (B); N-benzoyl-L-alanine methyl ester can be adsorbed both at site A and at site B. However, substitution of the split-off group in the substrates previously adsorbed at site B by the p-nitrophenyl group causes their transfer to site A.
Online Inquiry
Verification code
Inquiry Basket