5037-75-2

Basic information

• Product Name: Cyclo(Phe-Gly)
• Synonyms: Cyclo(Phe-Gly)
• CAS NO: 5037-75-2
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.22518
• Mol File: 5037-75-2.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 535.1°Cat760mmHg
• Flash Point: 242.8°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 1.59E-11mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: Cyclo(Phe-Gly)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclo(Phe-Gly)(5037-75-2)
• EPA Substance Registry System: Cyclo(Phe-Gly)(5037-75-2)

Safety Data

• Hazardous Substances Data: 5037-75-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12N2O2/c14-10-7-12-11(15)9(13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,15)(H,13,14)

Upstream product

• 5513-69-9 benzyloxycarbonyl-glycyl-L-phenylalanine amide 
• 5184-17-8 N-benzyloxycarbonyl-L-phenylalanylglycine methyl ester 
• 721-90-4 L-phenylalanylglycine 
• 19240-24-5 N--L-3-phenylalanine methyl ester hydrochloride 
• 145615-35-6 metronidazole glycyl phenylalaninate hydrochloride 
• 65559-51-5 L-Phenylalaninyl-glycine methyl ester 
• 30189-51-6 ethyl (N-tert-butoxycarbonyl-L-phenylalanyl)glycinate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 7625-57-2 methyl 2-((2S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)acetate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 98675-14-0 N-(N-tert-butoxycarbonyl-glycyl)-phenylalanine ethyl ester 
• 64991-29-3 tert-butyl (2S)-2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-3-phenylpropanoate 
• 1160857-01-1 9-{[2-(O-phenylalanylglycyl)hydroxyethoxy]methyl}guanine trifluoroacetic acid 
• 106624-70-8 methyl (2S)-2-[[2-(t-butoxycarbonylamino)acetyl]amino]-3-phenylpropanoate 

Downstream Products

• 76982-22-4 cyclo-N,N'-diacetyl- 
• 265096-24-0 (4S)-4-Benzyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione 
• 374114-75-7 (S)-1-(2-Azido-benzoyl)-6-benzyl-piperazine-2,5-dione 
• 117249-51-1 (R)-3-benzyl-(Z)-6-benzylidene-2,5-piperazinedione 
• 77027-33-9 4-acetyl-(S)-3-benzyl-(E)-6-benzylidene-2,5-piperazinedione 
• 77027-29-3 4-acetyl-(S)-3-benzyl-(Z)-6-benzylidene-2,5-piperazinedione 
• 208655-19-0 (S)-2-Benzylpiperazine 
• 959865-80-6 (S)-3-benzyl-1,4-di(tert-butoxycarbonyl)piperazine-2,5-dione 
• 1235977-31-7 t-butyl-3-[(3S)-(Z)-(5-benzyl-3,6-dioxopiperazin-2-ylidene)methyl]-4-nitroindole-1-carboxylate 
• 95713-60-3 L-Phe-L-FDAA 

Relevant articles and documents

Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization

Through a screen of over one hundred and 30 permutations of reaction temperatures, solvents, carbodiimide resins, and carbodiimide molar equivalences, in the presence, absence, or combination of diisopropylamine and benzotriazole additives, a convenient and first reported carbodiimide polymer-assisted flow approach to effect amide coupling and lactamization was developed. The protocol entails injecting a single solution (1:9 dimethylformamide: dichloromethane) containing a carboxylic acid and an amine or linear peptide sequence into a continuous stream of dichloromethane. The protocol remained viable in the absence of base, did not require carboxylate preactivation which, and in concert with minimal workup requirements, enabled the isolation of products in high yields. Compared to the utilization of untethered carbodiimide reagents, the flow procedure was also observed to provide a degree of racemization safety.

Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure–activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.