Boc-D-citrulline
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Boc-D-citrulline

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Category
BOC-Amino Acids
Catalog number
BAT-007080
CAS number
121080-95-3
Molecular Formula
C11H21N3O5
Molecular Weight
275.30
Boc-D-citrulline
IUPAC Name
(2R)-5-(carbamoylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-D-Cit-OH; (R)-2-Boc-amino-5-ureidopentanoic acid; Boc-D-Orn(carbamoyl)-OH; Boc D Cit OH
Appearance
White crystalline powder
Purity
≥ 98% (NMR)
Density
1.2±0.1 g/cm3
Boiling Point
483.0±45.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H21N3O5/c1-11(2,3)19-10(18)14-7(8(15)16)5-4-6-13-9(12)17/h7H,4-6H2,1-3H3,(H,14,18)(H,15,16)(H3,12,13,17)/t7-/m1/s1
InChI Key
CMJCWQISQGNHHI-SSDOTTSWSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCCNC(=O)N)C(=O)O

Boc-D-citrulline, a derivative of the amino acid citrulline, finds extensive use in research and biotechnological fields. Here are four key applications of Boc-D-citrulline:

Peptide Synthesis: A cornerstone of solid-phase peptide synthesis, Boc-D-citrulline acts as a protected amino acid derivative. The Boc protecting group shields citrulline’s amino group, preventing premature reactions during peptide chain construction. This method heightens the efficiency and precision of peptide and protein synthesis, pivotal for advancements in structural biology and drug discovery.

Drug Development: Nestled within the realm of therapeutic peptide creation, Boc-D-citrulline imparts crucial contributions. By integrating Boc-D-citrulline into peptide sequences, researchers can scrutinize citrulline-containing peptides’ impact on biological systems. This proves instrumental in formulating medications for ailments like cardiovascular diseases and immune disorders, where citrulline metabolism holds significance.

Protein Engineering: Powering the realm of protein engineering, Boc-D-citrulline facilitates the incorporation of non-standard amino acids into proteins, reshaping their structure and functionality. Through precise placement of Boc-D-citrulline residues, scientists engineer proteins boasting novel traits or heightened stability. This method is instrumental in crafting enzymes with superior catalytic functions and proteins with augmented therapeutic efficacy.

Analytical Chemistry: Within the realm of analytical chemistry, Boc-D-citrulline assumes a vital role in methods like high-performance liquid chromatography (HPLC). It serves as a catalyst for studying amino acid composition and metabolism, acting as a standard or derivative in biological sample analysis. This function aids in accurately quantifying citrulline levels, a critical element in metabolic research and clinical diagnostics, especially concerning conditions linked to urea cycle disorders.

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