40216-83-9

Basic information

• Product Name: trans-4-Hydroxy-L-proline methyl ester hydrochloride
• Synonyms: H-HYP-OME HCL;H-L-HYP-OME HCL;HYDROXYPROLINE-OME HCL;L-4-HYDROXYPROLINE METHYL ESTER HYDROCHLORIDE;L-4-HYDROXYPROLINE METHYL ESTER HYDROCHLORIDE SALT;L-4-TRANS-HYDROXYPROLINE METHYL ESTER HYDROCHLORIDE;L-4-TRANS-HYDROXYPROLINE METHYL ESTER HYDROCHLORIDE SALT;L-TRANS-4-HYDROXYPROLINE METHYL ESTER HYDROCHLORIDE SALT
• CAS NO: 40216-83-9
• Molecular Formula: C₆H₁₁NO₃*ClH
• Molecular Weight: 181.62
• EINECS: 1533716-785-6
• Product Categories: Nitrogen cyclic compounds;Amino Acid Derivatives;Amino Acids;Hydroxyproline [Hyp];Peptide Synthesis;Proline Derivatives;Unnatural Amino Acid Derivatives;Amino Acids & Derivatives;Chiral Reagents;Heterocycles
• Mol File: 40216-83-9.mol

Chemical Properties

• Melting Point: 169 °C
• Boiling Point: 247.2ºC at 760 mmHg
• Flash Point: 103.3ºC
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• Stability: Hygroscopic
• BRN: 4716932
• CAS DataBase Reference: trans-4-Hydroxy-L-proline methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Hydroxy-L-proline methyl ester hydrochloride(40216-83-9)
• EPA Substance Registry System: trans-4-Hydroxy-L-proline methyl ester hydrochloride(40216-83-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 40216-83-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trans-4-Hydroxy-L-proline methyl ester hydrochloride is used as an active pharmaceutical ingredient for the development of drugs targeting various medical conditions. Its presence in structural proteins like collagen and elastin makes it a promising candidate for treatments related to connective tissue disorders and wound healing.
Used in Cosmetic Industry:
In the cosmetic industry, trans-4-Hydroxy-L-proline methyl ester hydrochloride is used as an ingredient in skincare products for its potential benefits in promoting skin elasticity and reducing the signs of aging. Its role in collagen and elastin production may contribute to improved skin firmness and a more youthful appearance.
Used in Research and Development:
Trans-4-Hydroxy-L-proline methyl ester hydrochloride is also utilized in research and development for its potential applications in the study of protein structure, function, and interactions. As a derivative of a naturally occurring amino acid, it can be used to investigate the role of specific amino acids in protein folding, stability, and biological activity.
Used in Nutritional Supplements:
trans-4-Hydroxy-L-proline methyl ester hydrochloride may also be used as an additive in nutritional supplements, particularly those aimed at supporting connective tissue health and promoting the synthesis of collagen and elastin. Its inclusion in these products could potentially offer benefits for individuals seeking to improve their skin, joint, and overall tissue health.

InChI:InChI=1/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

Upstream product

• 67-56-1 methanol 
• 51-35-4 4R-4-hydroxyproline 
• 77-76-9 2,2-dimethoxy-propane 
• 75-36-5 acetyl chloride 
• 51-35-4 4-hydroxyproline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 32968-78-8 (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid hydrochloride 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 

Downstream Products

• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 67943-19-5 methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 164167-01-5 N-trityl-L-pyroglutamyl-D-histidyl(N^im-trityl)-trans-4-hydroxy-L-proline methyl ester 
• 164166-93-2 N-trityl-L-pyroglutamyl-L-histidyl(N^im-trityl)-trans-4-hydroxy-L-proline methyl ester 
• 179990-59-1 (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 195453-64-6 tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate 
• 195453-67-9 tert-butyl (2S)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate 
• 172947-80-7 (2S,4R)-1-ethyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 220060-02-6 Boc-Pro-Hyp-OMe 
• 220061-76-7 (2S,4R)-1-((R)-2-tert-Butoxycarbonylamino-propionyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 16257-57-1 methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 
• 16257-73-1 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 

Relevant articles and documents

4'-Methyloxycarbamyl-3'-deoxy-5-methyluridine; synthesis of a novel nucleoside analogue

The preparation of 4'-methyloxycarbamyl-3'-deoxythymidine from chiral amino acid precursors is described. The route chosen employs a hitherto unreported electrochemical oxidation of a suitably protected derivative of trans-4-hydroxy-L-proline, to obtain the key intermediate compound. Conventional condensation methodology is then used to arrive at the target nucleoside.

Synthesis and crystal structure of cis-4-azido-L-proline methyl ester hydrochloride

The key precursor for the synthesis of novel influenza neuraminidase inhibitors, cis-4-azido-L-proline methyl ester hydrochloride (C6H 11ClN4O2, Mr = 206.63), was prepared as white needle-shaped crystals and its structure was elucidated by single-crystal X-ray diffraction. In the crystal structure, molecules are linked through intermolecular hydrogen bonds, forming layers perpendicular to the bc plane.

VISUAL DETECTION OF PBD INDUCED DNA CROSSLINKS

The present invention relates to the field of oncology, laboratory tools and methods, and especially anti-tumor DNA crosslinking agents. Most patients with advanced solid tumors develop resistance to chemotherapy due to the ability of cancer cells to repair or tolerate sustained DNA damages. The inventors showed that the compounds according to the present invention allow the detection and visualization of alkylated DNA damages induced by PBDs without altering their DNA crosslinking ability. This enables the study of the effect and properties of PBDs. In particular, the present invention relates new derivates of PBD molecules and their synthesis. The present invention also relates to a method for visualizing DNA crosslinking; to a method for assessing the resistance of a tumor to a crosslinking agent and to a method for identifying a molecule or treatment for improving the efficiency of a crosslinking agent.

Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe

As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(L-Pro-L-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(L-Pro-L-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide-and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine-and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG

PROBLEM TO BE SOLVED: To provide: a method for producing a connected body; a method for using the connected body in the production of a uniform conjugate; and a method for applying the conjugate in the treatment of cancer, infectious diseases, and autoimmune diseases. SOLUTION: A novel connected body is provided that includes a 2,3-di-substituted succinic acid group or a 2-mono-substituted or 2,3-di-substituted fumaric acid or maleic acid (trans (E)- or cis (Z)-butenedioic acid) group for conjugating 2 or more compounds/cytotoxic agents per connected body with a cell-binding molecule by specifically bridge-linking to a pair of thiol on the cell-binding molecule. The connected body is exemplified by the following general formula. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Amphiphilic immobilized diphenylprolinol alkyl ether catalyst on PS-PEG resin

Diphenylprolinol silyl ether is a widely used organocatalyst, and its immobilization on a solid support was investigated for the easy recycling and reuse of this catalyst. Because a silyl ether bond of the catalyst is weak, its alkyl ether was attached to polymers such as a polyquinoxaline-based polymer, a polystyrene polymer (PS) resin, and a polystyrenepoly(ethylene glycol) graft copolymer (PS-PEG) resin. Although a polymer-supported organocatalyst generally decreases its reactivity compared with the monomer catalyst, diphenylprolinol anthrylmethyl ether supported on PS-PEG was found to be a reactive organocatalyst; it catalyzed the Michael reaction of an aldehyde and a nitroalkene in water without an organic solvent being present, with excellent diastereo- and enantioselectivities.

Quinoline-Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

A series of novel quinoline-proline hybrids (11a-g) and quinoline-proline-1,2,3-triazole hybrids (12-14) were synthesized by click chemistry based on molecular hybridization concept and were characterized by NMR, mass spectrometry, and elemental analysis. All the titled target compounds were tested for antitubercular activity by MABA and LORA methods by in vitro. Interestingly, two compounds (2R,4S)-1-((2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-methyl)-4-(4-nitrobenzamido)-N-phenylpyrrolidine-2-carboxamide (11b) and (2R,4S)-1-((2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-methyl)-4-(4-fluorobenzamido)-N-phenylpyrrolidine-2-carboxamide (11c) exhibited significant activity against the tested Mycobacterium tuberculosis H37Rv strain. Further, the cytotoxicity (CC50) profile of the titled compounds against the Vero cell was performed and discussed. A molecular docking study of the hit compounds (11b and 11c) was also performed to find their putative binding interaction with the active site of the target proteins. Finally, in silico ADMET properties were also predicted for all the synthesized molecules to evaluate their drug-likeness behavior.

BI-FUNCTIONAL COMPOUNDS AND METHODS FOR TARGETED UBIQUITINATION OF ANDROGEN RECEPTOR

The present invention relates to bi-functional compounds which function to recruit endogenous proteins to an E3 ubiquitin ligase for degradation, and methods for using same. More specifically, the present disclosure provides specific proteolysis targeting chimera (PROTAC) molecules which find utility as modulators of targeted ubiquitinization of a variety of polypeptides and other proteins, in particular the androgen receptor of a slice variant of AR which lacks the LBD, labelled as AR-V7, which are then degraded and/or otherwise inhibited by the compounds as described herein.

CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES

A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

Amino acid conjugates of 2-mercaptobenzimidazole provide better anti-inflammatory pharmacology and improved toxicity profile

Benzimidazole is an important pharmacophore for clinically active drugs against inflammation and treatment of pain, however, it is associated with gastrointestinal side effects. Here we synthesized benzimidazole based agents with significant analgesic/anti-inflammatory potential but with less gastrointestinal adverse effects. In this study, we synthesized novel, orally bioavailable 2-mercaptobenzimidazole amino acid conjugates (4a–4o) and screened them for analgesic, anti-inflammatory and gastro-protective effects. The synthesized 2-mercaptbenzimidazole derivatives were characterized for their structure using FTIR, 1H NMR and 13C NMR spectroscopic techniques. The 2-mercaptobenzimidazole amino acid conjugates have found to possess potent analgesic, anti-inflammatory and gastroprotective activities, particularly with compound 4j and 4k. Most of the compounds exhibited remarkable anti-ulcer and antisecretory effects. Molecular docking studies were carried out to study the binding affinities and interactions of the synthesized compounds with target proteins COX-2 (PDB ID: 3LN1) and H+/K+-ATPase (PDB ID: 5Y0B). Our results support the clinical promise of these newly synthesized 2-mercaptobezimidazol conjugates as a component of therapeutic strategies for inflammation and analgesia, for which the gastric side effects are always a major limitation.