L-Homocitrulline
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L-Homocitrulline

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Category
L-Amino Acids
Catalog number
BAT-005584
CAS number
1190-49-4
Molecular Formula
C7H15N3O3
Molecular Weight
189.22
L-Homocitrulline
IUPAC Name
(2S)-2-amino-6-(carbamoylamino)hexanoic acid
Synonyms
L-HomoCit-OH; Nε-Carbamoyl-L-lysine; (S)-2-Amino-6-ureidohexanoic acid
Related CAS
96386-92-4 (hydrochioride)
Purity
≥ 99% (TLC)
Density
1.241g/cm3
Boiling Point
393°C at 760mmHg
Storage
Store at 2-8°C
InChI
InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1
InChI Key
XIGSAGMEBXLVJJ-YFKPBYRVSA-N
Canonical SMILES
C(CCNC(=O)N)CC(C(=O)O)N

L-Homocitrulline is a non-proteinogenic amino acid, structurally similar to citrulline, a known intermediary in the urea cycle. Unlike citrulline, L-homocitrulline is characterized by an additional methylene group, which distinguishes its chemical structure and potential biological roles. This amino acid is not synthesized in the human body under normal metabolic conditions but is often formed through post-translational modification or as a result of certain metabolic disorders. The presence of L-homocitrulline in the human body can thus serve as a biochemical marker for various physiological and pathological states. The detection and quantification of this amino acid offer insights into metabolic pathways and are useful in the field of clinical diagnostics.

One of the primary applications of L-homocitrulline is in the field of nephrology, particularly concerning kidney function assessments. Its levels in the blood and urine are indicative of renal tubular disorders and are often used as a diagnostic marker to evaluate kidney health. In cases of chronic kidney disease or other renal impairments, the levels of L-homocitrulline can be significantly altered, providing clinicians with valuable information regarding the progression and severity of the condition. Moreover, research has suggested that L-homocitrulline levels might correlate with the effectiveness of certain interventions aimed at improving renal function, thus playing a role in treatment monitoring.

In the realm of cardiology, L-homocitrulline has garnered attention for its connection to cardiovascular health. Elevated levels have been associated with endothelial dysfunction, a precursor to atherosclerosis and other cardiovascular conditions. Consequently, measuring L-homocitrulline can serve as a predictive marker for cardiovascular risk assessment in patients. Furthermore, due to its relationship with metabolic pathways related to nitric oxide production, L-homocitrulline is also being explored for its therapeutic potential in managing conditions like hypertension and other related disorders. This potential makes it a subject of intense study for developing new cardiovascular treatments.

The study of autoimmune diseases is another critical area where L-homocitrulline has found relevance. Its involvement in the modification of proteins to produce homocitrullinated peptides can trigger immune responses, making it significant in diseases like rheumatoid arthritis. The immune system’s recognition of these peptides as foreign can lead to chronic inflammation and joint damage, hallmarks of autoimmune pathologies. Thus, L-homocitrulline is essential in understanding the mechanisms underlying such diseases and developing diagnostic tools and therapeutic strategies to combat them. Its role as a molecular marker in autoimmune processes highlights its potential utility in clinical settings.

Lastly, L-homocitrulline is of interest in the study of neurodegenerative diseases. Researchers are exploring its potential impact on neurological health, given its presence in brain tissue and its abnormal accumulation in certain neurological disorders. The disruption of normal amino acid processing in the brain may lead to the buildup of L-homocitrulline, contributing to neuronal damage and the progression of diseases such as Alzheimer’s or Parkinson’s. As such, its examination is crucial in developing new biomarkers for early detection and monitoring of neurodegenerative conditions, paving the way for novel therapeutic approaches targeting amino acid metabolism in the brain.

2. Absorption of homocitrulline from the gastrointestinal tract
D F Evered, J V Vadgama Br J Nutr. 1983 Jan;49(1):35-42. doi: 10.1079/bjn19830008.
1. Transport of L-homocitrulline, an amino acid which occurs in milk products, was studied with rat small intestine in vitro and from the human mouth in vivo. Absorption was partially dependent, in both systems, on the presence of sodium ions. 2. Metabolic inhibitors decreased L-homocitrulline uptake across the small intestine. Transport across the intestine did not occur against the concentration gradient but did show saturation kinetics. 3. The barbiturate, amytal, did not inhibit buccal absorption. Saturation kinetics were demonstrated. 4. Experiments were conducted with L-citrulline, or other amino acids, as possible inhibitors of L-homocitrulline transport. Results were compatible with Na+-dependent carrier-mediated uptake across the buccal mucosa. Active transport could be involved with the small intestine assuming that L-homocitrulline has a low affinity for the carrier system.
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