CYCLO(-GLY-PHE)

Base Information

• Chemical Name: CYCLO(-GLY-PHE)
• CAS No.: 10125-07-2
• Molecular Formula: C11H12 N2 O2
• Molecular Weight: 204.228
• Mol file: 10125-07-2.mol

Synonyms:2,5-Piperazinedione,3-(phenylmethyl)-, (S)-; 2,5-Piperazinedione, 3-benzyl-, L- (8CI);Cyclo(glycyl-L-phenylalanyl) (8CI); (S)-2-Benzylpiperazine-3,6-dione;(S)-3-Benzyl-2,5-dioxopiperazine; (S)-3-Benzylpiperazine-2,5-dione; Cyclicglycylphenylalanine; Cyclic(glycylphenylalanyl); Cyclo(Gly-L-Phe);Cyclo(Gly-Phe); Cyclo(L-phenylalanylglycine); Cyclo(L-phenylalanylglycyl);Cyclo-glycyl-L-phenylalanine

Chemical Property of CYCLO(-GLY-PHE)

Chemical Property:

• Melting Point: 266-268℃
• Boiling Point: 535.1±43.0 °C(Predicted)
• PKA: 13.18±0.40(Predicted)
• Density: 1.202
• Storage Temp.: -15°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclo(-Gly-Phe) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Cyclo(-Gly-Phe) is used to study the thermodynamics of protein unfolding. It is also able to cause gelation in a wide variety of organic fluids, including edible oils, glyceryl esters, alcohols, and aromatic molecules.

Technology Process of CYCLO(-GLY-PHE)

There total 59 articles about CYCLO(-GLY-PHE) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(Z)-3-phenylmethylenepiperazine-2,5-dione (19459-03-1) → cyclo(Gly-Phe) (5037-75-2,10125-07-2,23927-19-7)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (R,R)-f-spiroPhos; hydrogen; In dichloromethane; at 30 ℃; for 6h; under 15201 Torr; enantioselective reaction; Glovebox;

DOI:10.1021/acs.orglett.1c01894

Reference yield: 99.0%

tert-butyl (2S)-2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-3-phenylpropanoate (64991-29-3) → cyclo(Gly-Phe) (5037-75-2,10125-07-2,23927-19-7)

Guidance literature:

In water; at 250 ℃; for 0.166667h; under 7757.43 Torr; Microwave irradiation;

DOI:10.3390/molecules14082836

Reference yield: 97.0%

(S)-PheGly (721-90-4) → cyclo(Gly-Phe) (5037-75-2,10125-07-2,23927-19-7)

Guidance literature:

With (3-{[(cyclohexylimino)methylidene]amino}propyl)oxy linked polystyrene resin; In dichloromethane; N,N-dimethyl-formamide; for 0.0833333h; Flow reactor;

DOI:10.1021/acscombsci.0c00001

upstream raw materials:

benzyloxycarbonyl-glycyl-L-phenylalanine amide

N-benzyloxycarbonyl-L-phenylalanylglycine methyl ester

L-phenylalanylglycine

N--L-3-phenylalanine methyl ester hydrochloride

Downstream raw materials:

(S)-2-Benzylpiperazine

(+/-)-1,4-diacetyl-3-benzylpiperazine-2,5-dione

t-butyl-3-[(3S)-(Z)-(5-benzyl-3,6-dioxopiperazin-2-ylidene)methyl]-4-nitroindole-1-carboxylate

L-Phe-L-FDAA

Refernces

• 1、 Conic, Dragan,De Azambuja, Francisco,Harvey, Jeremy N.,Loosen, Alexandra,Parac-Vogt, Tatjana N.,Van Den Besselaar, Maxime. "En Route to a Heterogeneous Catalytic Direct Peptide Bond Formation by Zr-Based Metal-Organic Framework Catalysts". . p. 7647 - 7658. Retrieved 2021.
• 2、 Pickenhagen et al.. "-". . p. 1078,1084. Retrieved 1975.
• 3、 Nitecki,D.E. et al.. "-". . p. 864 - 866. Retrieved 1968.
• 4、 Xiao, Guiying,Xu, Shuang,Xie, Chaochao,Zi, Guofu,Ye, Weiping,Zhou, Zhangtao,Hou, Guohua,Zhang, Zhanbin. "Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation". supporting information. p. 5734 - 5738. Retrieved 2021/08/01.