Fmoc-D-citrulline
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Fmoc-D-citrulline

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Category
Fmoc-Amino Acids
Catalog number
BAT-007412
CAS number
200344-33-8
Molecular Formula
C21H23N3O5
Molecular Weight
397.42
Fmoc-D-citrulline
IUPAC Name
(2R)-5-(carbamoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Synonyms
Fmoc-D-Cit-OH; (R)-2-Fmoc-amino-5-ureidopentanoic acid; Fmoc-D-Orn(carbamoyl)-OH; Fmoc D Cit OH
Related CAS
133174-15-9 (L-isomer)
Appearance
White solid
Purity
≥ 99% (HPLC)
Density
1.316±0.06 g/cm3
Melting Point
148-160 °C
Boiling Point
671.5±55.0 °C
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-/m1/s1
InChI Key
NBMSMZSRTIOFOK-GOSISDBHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCNC(=O)N)C(=O)O

Fmoc-D-citrulline, a versatile protected amino acid widely utilized in peptide synthesis and research, offers a multitude of applications. Here are four key applications of Fmoc-D-citrulline:

Peptide Synthesis: A cornerstone of solid-phase peptide synthesis (SPPS), Fmoc-D-citrulline plays a pivotal role as a fundamental building block, enabling the construction of intricate peptide sequences. The Fmoc-protection strategy facilitates selective deprotection and coupling steps, crucial for the precise generation of peptides utilized across diverse fields such as biochemical research, drug development, and therapeutics.

Protein Engineering: Through the utilization of Fmoc-D-citrulline, researchers can engineer peptides and proteins with specialized functions, introducing unique structural and functional properties distinct from naturally occurring L-amino acids. By incorporating D-citrulline residues, scientists can craft proteins with enhanced stability, resistance to enzymatic degradation, or novel biological activities, pushing the boundaries of protein design.

Immunology Studies: In the domain of immunology, Fmoc-D-citrulline plays a vital role in synthesizing antigenic peptides for the study of autoimmunity and immune responses. Citrullinated peptides, particularly pertinent in investigations related to rheumatoid arthritis, act as crucial autoantigens. These synthesized peptides aid in unraveling the mechanisms underlying autoimmune diseases and in creating diagnostic tools to improve disease detection and management.

Medicinal Chemistry: In the realm of drug discovery, Fmoc-D-citrulline finds application in synthesizing peptidomimetics and peptide-based drugs. The incorporation of D-citrulline can enhance the pharmacokinetic properties of peptides, boosting features such as half-life and binding affinity. This characteristic positions Fmoc-D-citrulline as a valuable component in the development of novel therapeutic agents, underscoring its significance in advancing medicinal chemistry.

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