Boc-L-citrulline
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Boc-L-citrulline

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Category
BOC-Amino Acids
Catalog number
BAT-007103
CAS number
45234-13-7
Molecular Formula
C11H21N3O5
Molecular Weight
275.30
Boc-L-citrulline
IUPAC Name
(2S)-5-(carbamoylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-L-Cit-OH; (S)-2-Boc-amino-5-ureidopentanoic acid; Boc-L-Orn(carbamoyl)-OH; Boc L Cit OH
Appearance
White to pale yellow powder
Purity
≥ 98% (TLC)
Density
1.212±0.06 g/cm3
Melting Point
60 °C
Boiling Point
483.0±45.0 °C at 760 mmHg
Storage
Store at -20 °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-/m0/s1
InChI Key
CMJCWQISQGNHHI-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCCNC(=O)N)C(=O)O

Boc-L-citrulline, a derivative of the amino acid citrulline prevalent in biochemical and medical research, boasts diverse applications.

Peptide Synthesis: Renowned for its stability and ease of integration, Boc-L-citrulline serves as a cornerstone in peptide synthesis. The strategic protection of its amino group with a Boc (tert-butyloxycarbonyl) shield facilitates the sequential addition of amino acids. This meticulous process culminates in the meticulous assembly of peptide chains, primed for both research endeavors and therapeutic purposes.

Drug Development: Boc-L-citrulline assumes a pivotal role in crafting therapeutic agents, especially those targeting the urea cycle. By incorporating Boc-L-citrulline into drug candidates, researchers can delve into its impact on nitric oxide production and vasodilation. This research is imperative for the formulation of cardiovascular medications and supplements, propelling advancements in the realm of pharmacology.

Biochemical Research: Delving into enzymatic pathways involving citrulline, researchers utilize Boc-L-citrulline as a potent tool in biochemical research. The judicious application of the Boc-protective group allows for targeted studies sans unwanted side reactions. This approach aids in unraveling the intricacies of metabolic processes and enzyme mechanisms at a granular level, shedding light on the molecular underpinnings of these biological phenomena.

Cell Culture Studies: Embarking on cell culture experiments, Boc-L-citrulline emerges as a crucial component in exploring its effects on cellular metabolism and nitric oxide synthesis. Incorporating it into culture media enables researchers to decipher cellular responses and signaling pathways. This utilization proves invaluable in preclinical research, offering deeper insights into cell physiology and potential avenues for therapeutic interventions.

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