2578-57-6

Basic information

• Product Name: H-PRO-GLY-OH
• Synonyms: prolylglycine;PRO-GLY MONOHYDRATE;PRO-GLY;L-PRO-GLN;L-PROLYLGLYCINE;H-PRO-GLY-OH;Glycine, L-prolyl- (9CI);2-(prolylamino)acetic acid
• CAS NO: 2578-57-6
• Molecular Formula: C₇H₁₂N₂O₃
• Molecular Weight: 172.18
• Product Categories: PYRROLE;Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 2578-57-6.mol

Chemical Properties

• Melting Point: 236℃
• Boiling Point: 468.5 °C at 760 mmHg
• Flash Point: 237.1 °C
• Appearance: White to off white powder
• Density: 1.266 g/cm³
• Vapor Pressure: 4.5E-10mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: −20°C
• CAS DataBase Reference: H-PRO-GLY-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-PRO-GLY-OH(2578-57-6)
• EPA Substance Registry System: H-PRO-GLY-OH(2578-57-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2578-57-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-PRO-GLY-OH is used as a substrate for prolinase (prolyl dipeptidase) due to its dipeptide structure, which is essential for the study and development of drugs targeting this enzyme. This application is crucial in understanding the enzyme's role in various biological processes and its potential as a therapeutic target.
Used in Research and Development:
H-PRO-GLY-OH serves as a valuable compound in the field of research and development, particularly in the study of enzyme kinetics, protein-ligand interactions, and the development of novel inhibitors or activators for prolinase. Its unique structure allows researchers to explore its potential in modulating enzyme activity and understanding the underlying mechanisms.
Used in Chemical Synthesis:
As a dipeptide, H-PRO-GLY-OH can be utilized as a building block in the synthesis of more complex peptides and proteins. This application is particularly relevant in the fields of biotechnology and materials science, where the development of novel bioactive molecules and materials with specific properties is of great interest.
Used in Cosmetics Industry:
Due to its dipeptide nature and potential effects on skin health, H-PRO-GLY-OH may find applications in the cosmetics industry as an ingredient in anti-aging or skin repair products. Its ability to modulate enzyme activity could potentially contribute to improved skin health and appearance.

Purification Methods

Recrystallise L-prolylglycine from water at 50-60o by addition of EtOH. [Appel et al. Chem Ber 108 2680 1975, Rydon & Smith J Chem Soc 3642 1956.]

InChI:InChI=1/C7H12N2O3/c10-6(11)4-9-7(12)5-2-1-3-8-5/h5,8H,1-4H2,(H,9,12)(H,10,11)/t5-/m0/s1

Upstream product

• 3705-27-9 (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 1911-74-6 N-Trt-Pro 
• 92466-15-4 N-trityl-proline succinimide ester 
• 92466-05-2 Trt-Pro-Gly-OBzl 
• 28310-65-8 N-tert-butyloxycarbonyl-proline p-nitrophenyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 2966-05-4 (S,S)-N-trifluoroacetylproline anhydride 
• 147-85-3 L-proline 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 33256-35-8 H-Pro-Gly-OMe 
• 34290-72-7 tert-butyloxycarbonyl-prolyl-glycine methyl ester 
• 2766-31-6 ethyl (N-benzoxycarbonyl-L-prolyl)glycinate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Downstream Products

• 2441-81-8 N-[1-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-glycine 
• 19179-12-5 Hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 
• 2766-18-9 N-carbobenzoxyprolylglycine 
• 3705-27-9 (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 56-40-6 glycine 
• 147-85-3 L-proline 
• 112471-80-4 N,O-bis-CBZ-5-amino-N-(hydroxymethyl)pentanamide 
• 675-20-7 piperidin-2-one 
• 85651-86-1 N-tert-butyloxycarbonyl-O-benzyl-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolylglycyl-L-prolyl-L-isoleucine 
• 85642-26-8 N-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolylglycyl-L-prolyl-L-isoleucine 
• 85642-28-0 tert-butyl N-tert-butyloxycarbonyl-L-prolyl-L-phenylalanyl-L-prolylglycyl-L-prolyl-L-isoleucinate 
• 77654-52-5 L-prolyl-L-phenylalanyl-L-prolylglycyl-L-prolyl-L-isoleucine 
• 82289-41-6 des-Tyr¹-β-casomorphin-5 
• 47283-59-0 L-phenylalanyl-L-prolylglycine 

Relevant articles and documents

Leonurine derivative and application thereof in preparing medicine for preventing or treating ischemic cerebrovascular diseases

The invention provides a leonurine derivative and application of the leonurine derivative in preparation of a medicine for preventing or treating ischemic cerebrovascular diseases. The leonurine derivative has a structure as shown in a general formula (I), wherein X is selected from O or NH; Y is selected from any one of natural amino acid, substituted amino acid or amino alcohol; Z is selected from H, proline and any substituted proline. Pharmacological experiments prove that the leonurine derivative provided by the invention has the effects of neuroprotection, cerebral infarction area reduction and animal neurobehavioral scoring, and is good in safety, so that the leonurine derivative has important significance for developing novel medicines for preventing or treating ischemic cerebrovascular diseases.

Design, synthesis, and biological evaluation of novel stachydrine derivatives as potent neuroprotective agents for cerebral ischemic stroke

Stachydrine is a natural product with multiple protective biological activities, including those involved in preventing cancer, ischemia, and cardiovascular disease. However, its use has been limited by low bioavailability and unsatisfactory efficacy. To address this problem, a series of stachydrine derivatives (A1/A2/A3/A4/B1/B2/B3/B4) were designed and synthesized, and biological studies were carried out in vitro and in vivo. When compared with stachydrine, Compound B1 exhibited better neuroprotective effects in vitro, and significantly reduced infarction size in the model of the middle cerebral artery occlusion rat model. Therefore, Compound B1 was selected for further research on ischemic stroke. [Figure not available: see fulltext.].

Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe–Gly and Pro–Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through va

Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids

A general method for the synthesis of dipeptides has been developed, which does not require any coupling reagents. This method is based on the reaction of readily available HCl salts of amino acid methyl esters with tetrabutylphosphonium amino acid ionic liquids. The isolation procedure of stepwise treatment with AcOH is easy to carry out. The method was extended to the synthesis of tripeptide, tyrosyl-glycyl-glycine, present in IMREG-1, also.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: Catalyst, solvent, additive and temperature effects

A series of dipeptides of l-proline-l-amino acid and l-proline-d-amino acid were synthesized to evaluate the catalytic effect for asymmetric direct aldol reactions. In the direct aldol reaction, a catalyst of l-proline-l-amino acid achieves better enantioselectivity than the corresponding l-proline-d-amino acid catalyst. Solubility of the dipeptide catalysts in the solvents is a key point for achieving a better yield of the direct aldol reaction, while hydrogen bonding of solvent does not play an important role in attaining better enantioselectivity and yield. Yield and enantioselectivity of the direct aldol reaction in water were improved by NMM and SDS additives, but the results that were done in plain DMSO were even better.

Deprotection and cleavage of peptides bound to Merrifield resin by stable dimethyl ether-poly(hydrogen fluoride) (DMEPHF) complex, a new and convenient reagent for peptide chemistry

The newly developed stable DMEPHF (1/15) complex was found to be a highly effective reagent for the cleavage of peptides from Merrifield resins; ease of handling and its simple, complete removal from the reaction mixture make the reagent system a very useful HF equivalent for applications in solid-phase peptide synthesis.

PHOSPHONAMIDATE COMPOUNDS

Phosphonamidates of the formula STR1 wherein X is a substituted or unsubstituted imino or amino acid or ester. These compounds possess angiotensin converting enzyme activity and are thus useful as hypotensive agents.

SYNTHESIS AND CONFORMATION OF N-TRITYL DIPEPTIDE DERIVATIVES

N-Tritylamino acids activated with DCC/HOBt, were coupled with various amino acid derivatives without racemization.The trityl group was split off quantitatively in 10percent CCl3COOH monohydrate or CH2ClCOOH in CH2Cl2