Name: L-4-trans-Hydroxyproline methyl ester hydrochloride
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

L-Hyp-OMe HCl

IUPAC Name

methyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate;hydrochloride

Canonical SMILES

COC(=O)C1CC(CN1)O.Cl

InChI

InChI=1S/C6H11NO3.ClH/c1-10-6(9)5-2-4(8)3-7-5;/h4-5,7-8H,2-3H2,1H3;1H/t4-,5+;/m1./s1

InChIKey

KLGSHNXEUZOKHH-JBUOLDKXSA-N

Melting Point

161-172 °C

Appearance

White or off-white crystalline powder

Quantity

Data not available, please inquire.

Storage

Store at 2-8°C

Boiling Point

247.2°C at 760 mmHg

L-4-trans-Hydroxyproline methyl ester hydrochloride is a synthetic derivative of hydroxyproline, a key amino acid found in collagen and connective tissues. This compound is particularly useful in the study of protein structure and function, as it mimics natural hydroxyproline residues found in collagen. L-4-trans-Hydroxyproline methyl ester hydrochloride is widely used in peptide synthesis, particularly in the creation of collagen-related peptides, which are essential for studying the structure and stability of collagen fibers. This application is valuable in the fields of biochemistry, molecular biology, and structural proteomics, where understanding collagen's role in diseases such as osteogenesis imperfecta and fibrosis is critical.

One of the primary applications of L-4-trans-Hydroxyproline methyl ester hydrochloride is in the design and synthesis of collagen mimetic peptides. These peptides are used to model the secondary and tertiary structures of collagen, as hydroxyproline plays a crucial role in stabilizing the collagen triple helix. By incorporating this compound into peptide sequences, researchers can study the effects of hydroxyproline modifications on collagen stability and function. This application is particularly important in drug discovery, as it allows for the development of therapeutic strategies targeting collagen-related diseases such as osteoarthritis, wound healing disorders, and tissue fibrosis.

L-4-trans-Hydroxyproline methyl ester hydrochloride is also used in the development of biomaterials, particularly those aimed at mimicking the structural and mechanical properties of collagen. Due to its ability to incorporate into synthetic peptides or proteins, this compound can be used in tissue engineering applications to create scaffolds that resemble the extracellular matrix. These scaffolds are crucial for regenerative medicine, as they promote cell adhesion, growth, and differentiation. Researchers are exploring the use of L-4-trans-Hydroxyproline methyl ester hydrochloride-based materials for the development of advanced biomaterials used in wound healing, bone regeneration, and skin tissue engineering.

Another key application of L-4-trans-Hydroxyproline methyl ester hydrochloride is in the study of post-translational modifications of collagen. Hydroxyproline residues in collagen are often modified by enzymes like prolyl hydroxylase, and understanding these modifications is critical for determining the functional properties of collagen in tissues. By using this compound in in vitro studies, researchers can investigate how different forms of hydroxyproline affect the biochemical properties of collagen and its interactions with other extracellular matrix components. This knowledge could lead to the development of new therapies for diseases that involve collagen abnormalities, such as fibrosis or Ehlers-Danlos syndrome.

1. Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester

Andreea-Teodora Pânzariu, et al. Chem Cent J. 2016 Feb 4;10:6. doi: 10.1186/s13065-016-0151-6. eCollection 2016.

Background: l-Arginine is a semi-essential aminoacid with important role in regulation of physiological processes in humans. It serves as precursor for the synthesis of proteins and is also substrate for different enzymes such as nitric oxide synthase. This amino-acid act as free radical scavenger, inhibits the activity of pro-oxidant enzymes and thus acts as an antioxidant and has also bactericidal effect against a broad spectrum of bacteria. Results: New thiazolidine-4-one derivatives of nitro-l-arginine methyl ester (NO2-Arg-OMe) have been synthesized and biologically evaluated in terms of antioxidant and antibacterial/antifungal activity. The structures of the synthesized compounds were confirmed by (1)H, (13)C NMR, Mass and IR spectral data. The antioxidant potential was investigated using in vitro methods based on ferric/phosphomolybdenum reducing antioxidant power and DPPH/ABTS radical scavenging assay. The antibacterial effect was investigated against Gram positive (Staphylococcus aureus ATCC 25923, Sarcina lutea ATCC 9341) and Gram negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacterial strains. The antifungal activity was also investigated against Candida spp. (Candida albicans ATCC 10231, Candida glabrata ATCC MYA 2950, Candida parapsilosis ATCC 22019). Conclusions: Synthesized compounds showed a good antioxidant activity in comparison with the NO2-Arg-OMe. The antimicrobial results support the selectivity of tested compounds especially on P. aeruginosa as bacterial strain and C. parapsilosis as fungal strain. The most proper compounds were 6g (R = 3-OCH3) and 6h (R = 2-OCH3) which showed a high free radical (DPPH, ABTS) scavenging ability and 6j (R = 2-NO2) that was the most active on both bacterial and fungal strains and also it showed the highest ABTS radical scavenging ability.Graphical abstract1: ethyl 3-aminopropionate hydrochloride, 2a-j: aromatic aldehydes, 3: thioglycolic acid, 4a-j: thiazolidine-propionic acid derivatives , 5: Nω-nitro-L-arginine methyl ester hydrochloride, 6a-j: thiazolidine-propionyl-nitro-L-arginine methyl ester derivatives.

2. The Effects of Irisin on Nω-Nitro-L-arginine Methyl Ester Hydrochloride-Induced Hypertension in Rats

Nurettin Aydoğdu, Özlem Yalçınkaya Yavuz, Ebru Taştekin, Pınar Tayfur, Oktay Kaya, Nihayet Kandemir Balkan Med J. 2019 Oct 28;36(6):337-346. doi: 10.4274/balkanmedj.galenos.2019.2019.5.113. Epub 2019 Sep 5.

Background: The cause of about 95% of hypertension, an important public health problem, is unknown. Intensive studies are underway to understand the physiopathology of hypertension. Irisin, a newly discovered hormone, has been reported to dilate vascular smooth muscle and lower blood pressure acutely. Aims: To investigate the effects of chronic irisin treatment on blood pressure and renal functions in a hypertension model established by nitric oxide synthase inhibition by treatment with Nω-nitro-L-arginine methyl ester hydrochloride. Study design: Animal experimentation. Methods: Male Sprague-Dawley rats were divided into four groups (n=8). Control and irisin groups received an intravenous saline injection, hypertension and hypertension + irisin (hypertension + irisin) groups received 1.5 mg/100 g Nω-nitro-L-arginine methyl ester hydrochloride. Nω-nitro-L-arginine methyl ester hydrochloride (150 mg/L) was added to the drinking water of rats in groups hypertension and hypertension + irisin for three weeks. In the second week of the experiment, irisin (50 nmol/day) was given to rats in groups irisin and hypertension + irisin, and saline was administered to rats in groups control and hypertension for two weeks through subcutaneously placed osmotic minipumps. Blood pressure was measured by the tail-cuff plethysmography method. On the twenty-first day of the experiment, 24-hour urine, blood, and both kidneys of the rats were collected. Results: The hypertension group had elevated systolic, diastolic, and mean arterial blood pressure values compared with the control group, with decreased glutathione levels in tissue and serum, but an increase in serum oxidized glutathione level (p<0.05). Histopathologically, increased tubular injury, cast formation, glomerular sclerosis, and peritubular fibrosis levels were observed (p<0.05). Irisin treatment did not cause any significant change in blood pressure, renal functions, and injury scores. However, renal nitric oxide levels significantly increased, and endothelial nitric oxide synthase immunoreactivity was determined to be reduced (p<0.05). Conclusion: Treatment with chronic irisin at a physiological dose does not reduce blood pressure in an experimental model of hypertension. In different models of experimental hypertension, the effects of irisin administration at different doses and at different periods should be thoroughly investigated.