Fmoc-L-citrulline
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Fmoc-L-citrulline

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Category
Fmoc-Amino Acids
Catalog number
BAT-007441
CAS number
133174-15-9
Molecular Formula
C21H23N3O5
Molecular Weight
397.42
Fmoc-L-citrulline
IUPAC Name
(2S)-5-(carbamoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Synonyms
Fmoc-L-Cit-OH; (S)-2-Fmoc-amino-5-ureidopentanoic acid; Fmoc-L-Orn(carbamoyl)-OH; Fmoc L Cit OH
Related CAS
200344-33-8 (D-isomer)
Appearance
White powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.316 g/cm3
Melting Point
~ 160 °C
Boiling Point
671.5°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H23N3O5/c22-20(27)23-11-5-10-18(19(25)26)24-21(28)29-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,24,28)(H,25,26)(H3,22,23,27)/t18-/m0/s1
InChI Key
NBMSMZSRTIOFOK-SFHVURJKSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCNC(=O)N)C(=O)O

Fmoc-L-citrulline, a derivative of the amino acid citrulline, finds extensive utility in peptide synthesis and biochemical research.

Peptide Synthesis: Embedded within solid-phase peptide synthesis, Fmoc-L-citrulline acts as a facilitator for incorporating citrulline residues into peptide chains. The Fmoc (9-fluorenylmethyloxycarbonyl) group acts as a protective shield, selectively removable under gentle conditions to safeguard other functional groups within the peptide. A fundamental reagent, it is essential for scientists crafting bespoke peptides to probe protein interactions, enzyme activity, and myriad other intricate biochemical phenomena.

Biochemical Research: In the realm of biochemical research, Fmoc-L-citrulline plays a pivotal role in exploring post-translational modifications, especially citrullination - a process converting arginine residues to citrulline in proteins. This modification impacts diverse biological processes and disease pathways, including autoimmunity and cancer. Utilizing Fmoc-L-citrulline in these studies, scientists unravel the functions of citrullinated proteins, setting the stage for targeted therapeutic interventions that hold immense promise in combating complex diseases.

Enzyme Assays: Acting as a crucial substrate in assays measuring the activity of peptidylarginine deiminases (PADs), Fmoc-L-citrulline empowers researchers to monitor enzyme kinetics and activity under various conditions. This application is vital for drug discovery efforts aimed at identifying PAD inhibitors, crucial in diseases like rheumatoid arthritis. Through the use of Fmoc-L-citrulline in such assays, researchers gain insights into enzyme dynamics, contributing to the development of innovative treatment strategies that target key enzymatic pathways.

Pharmaceutical Development: Central to pharmaceutical research, Fmoc-L-citrulline plays a pivotal role in designing therapeutic peptides incorporating citrulline. These peptides may exhibit enhanced stability, bioavailability, or target specificity compared to their non-citrullinated counterparts. By integrating Fmoc-L-citrulline into the drug design process, researchers lay the groundwork for novel therapies that address diseases where citrullination emerges as a crucial molecular player, offering innovative solutions to complex health challenges.

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