Fmoc-L-homocitrulline
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Fmoc-L-homocitrulline

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Category
Fmoc-Amino Acids
Catalog number
BAT-007444
CAS number
201485-17-8
Molecular Formula
C22H25N3O5
Molecular Weight
411.45
Fmoc-L-homocitrulline
IUPAC Name
(2S)-6-(carbamoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
Synonyms
Fmoc-L-HomoCit-OH; Nα-Fmoc-Nε-carbamoyl-L-lysine; (S)-2-Fmoc-amino-6-ureidohexanoic acid; Fmoc L HomoCit OH
Related CAS
201485-38-3 (D-isomer)
Appearance
White to pale yellow powder
Purity
≥ 98% (HPLC)
Density
1.292±0.06 g/cm3
Melting Point
168-171 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H25N3O5/c23-21(28)24-12-6-5-11-19(20(26)27)25-22(29)30-13-18-16-9-3-1-7-14(16)15-8-2-4-10-17(15)18/h1-4,7-10,18-19H,5-6,11-13H2,(H,25,29)(H,26,27)(H3,23,24,28)/t19-/m0/s1
InChI Key
VJZUCXPETVPQIB-IBGZPJMESA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCCNC(=O)N)C(=O)O

Fmoc-L-homocitrulline, a derivative of the amino acid homocitrulline, finds primary utility in peptide synthesis and diverse research applications. Here are four key applications of Fmoc-L-homocitrulline:

Peptide Synthesis: Serving as a cornerstone in the realm of peptide synthesis, Fmoc-L-homocitrulline is instrumental in crafting homocitrullinated peptides crucial for delving into protein-protein interactions and post-translational modifications. This compound facilitates the incorporation of homocitrulline residues into peptide chains, shedding light on the structural and functional significance of this unique amino acid. These peptides become invaluable tools in biochemical assays and structural investigations, offering profound insights into the intricate landscape of disease mechanisms.

Immunology Research: Within the domain of immunology research, Fmoc-L-homocitrulline emerges as a key component in generating specialized antigens essential for eliciting antibodies against modified proteins. Homocitrulline-rich peptides play a pivotal role in deciphering autoimmune disorders like rheumatoid arthritis, where protein alterations hold sway. By generating precise antibodies, scientists embark on a quest to unravel the presence and impact of homocitrullinated proteins in the pathogenesis of diseases, unveiling novel avenues for therapeutic intervention.

Proteomics: Delving into the intricacies of proteomics, Fmoc-L-homocitrulline derivatives stand as indispensable tools for identifying and quantifying homocitrullinated proteins. Leveraging specialized mass spectrometry techniques, researchers unveil these modifications, offering glimpses into protein function and interaction within diverse biological milieus. This application proves critical in unraveling the maze of post-translational modifications and their profound effects on cellular signaling and function, paving the way for a deeper understanding of biological complexities.

Drug Development: At the forefront of drug development, Fmoc-L-homocitrulline emerges as a catalyst for innovation by being seamlessly integrated into peptide-based drugs. This incorporation elevates the stability, bioavailability, and targeted efficacy of these drugs, enhancing their therapeutic potential. By exploring the repercussions of homocitrulline integration, researchers navigate the realm of optimized peptide-based therapeutics.

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