Fmoc-D-homocitrulline
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Fmoc-D-homocitrulline

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Category
Fmoc-Amino Acids
Catalog number
BAT-007414
CAS number
201485-38-3
Molecular Formula
C22H25N3O5
Molecular Weight
411.45
Fmoc-D-homocitrulline
IUPAC Name
(2R)-6-(carbamoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
Synonyms
Fmoc-D-HomoCit-OH; Nα-Fmoc-Nε-carbamoyl-D-lysine; (R)-2-Fmoc-amino-6-ureidohexanoic acid; Fmoc D HomoCit OH
Related CAS
201485-17-8 (L-isomer)
Appearance
White to light yellow powder or crystals
Purity
≥ 95% (HPLC)
Melting Point
160-165 °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-/m1/s1
InChI Key
VJZUCXPETVPQIB-LJQANCHMSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCCNC(=O)N)C(=O)O

Fmoc-D-homocitrulline, a protected amino acid derivative, finds extensive utility in sophisticated peptide synthesis and various biochemical applications. Here are four key applications of Fmoc-D-homocitrulline:

Peptide Synthesis: Serving as a fundamental building block in custom peptide synthesis, Fmoc-D-homocitrulline plays a pivotal role in facilitating stepwise elongation of peptide chains under gentle conditions. Its Fmoc protecting group enables meticulous crafting of peptides for diverse research and therapeutic endeavors, showcasing its versatility and indispensability in the intricate world of peptide design.

Protein Engineering: Within the realm of protein engineering, the incorporation of Fmoc-D-homocitrulline into proteins unveils insights into structure-function relationships, offering a deeper understanding of protein folding, stability, and activity modulation. By strategically substituting this amino acid for its natural counterparts, researchers embark on a journey to design proteins with augmented or novel functionalities.

Drug Development: As a key player in the realm of peptide-based drug design, Fmoc-D-homocitrulline stands out for its capacity to enhance binding affinity and specificity towards target proteins, particularly those crucial for specific protein interactions. Leveraging its unique side chain properties, researchers harness its potential to craft highly specialized therapeutics with heightened efficacy.

Proteomics Research: In the intricate world of proteomics, Fmoc-D-homocitrulline emerges as a pivotal standard or marker in mass spectrometry analyses, offering invaluable insights into characterizing and quantifying complex protein mixtures. Its integration into peptide or protein samples aids in unraveling proteome dynamics, shedding light on potential disease biomarkers, and fueling breakthroughs in the quest for improved diagnostics and therapeutic strategies.

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