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2566-22-5

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2566-22-5 Usage

Chemical Properties

Crystalline

Uses

N-Benzoyl-L-phenylalanine is used in the preparation of α-di/monoketo ester derivatives of n-protected amino acids as inhibitors of cysteine of serine proteinases, as well as calpain inhibitors.

Definition

ChEBI: An N-acyl-L-phenylalanine that is L-phenylalanine in which one of the hydrogens of the amino group has been replaced by a benzoyl group.

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 2916, 1972 DOI: 10.1021/jo00983a034Tetrahedron Letters, 16, p. 4051, 1975

Check Digit Verification of cas no

The CAS Registry Mumber 2566-22-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,6 and 6 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2566-22:
(6*2)+(5*5)+(4*6)+(3*6)+(2*2)+(1*2)=85
85 % 10 = 5
So 2566-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C17H17NO3/c1-21-17(20)15(12-13-8-4-2-5-9-13)18-16(19)14-10-6-3-7-11-14/h2-11,15H,12H2,1H3,(H,18,19)/t15-/m0/s1

2566-22-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (H66608)  N-Benzoyl-L-phenylalanine, 98%   

  • 2566-22-5

  • 5g

  • 735.0CNY

  • Detail
  • Alfa Aesar

  • (H66608)  N-Benzoyl-L-phenylalanine, 98%   

  • 2566-22-5

  • 25g

  • 2940.0CNY

  • Detail

2566-22-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name BZ-PHE-OH

1.2 Other means of identification

Product number -
Other names BZO-PHE-OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2566-22-5 SDS

2566-22-5Relevant articles and documents

An expedient synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as jack bean urease inhibitors and free radical scavengers: Kinetic mechanism and molecular docking studies

Saeed, Aamer,Larik, Fayaz Ali,Channar, Pervaiz Ali,Mehfooz, Haroon,Ashraf, Mohammad Haseeb,Abbas, Qamar,Hassan, Mubashir,Seo, Sung-Yum

, p. 764 - 777 (2017)

In this study, some new azomethine-triazole hybrids 5a–5l derived from N-benzoyl-L-phenylalanine were synthesized and characterized. The synthesized compounds showed first-rate, urease inhibition, and compounds 5c and 5e were found to be most effective inhibitors with 0.0137?±?0.00082?μm and 0.0183?±?0.00068?μm, respectively (thiourea 15.151?±?1.27?μm). The kinetic mechanism of urease inhibition revealed the compounds 5c and 5e to be non-competitive inhibitors, whereas compounds 5d and 5j were found to be of mixed-type inhibitors. Docking studies also indicated better interaction patterns with urease enzyme. The results of enzyme inhibition, kinetic mechanism and molecular docking suggest that these compounds can serve as lead compounds in the design of more effective urease inhibitors.

-

Onuma et al.

, p. 3163,3164,3166 (1979)

-

OCCURRENCE AND BIOSYNTHESIS OF ASPERPHENAMATE IN SOLID CULTURES OF PENICILLIUM BREVICOMPACTUM

Bird, Bruce A.,Campbell, Iain M.

, p. 2405 - 2406 (1982)

The ester of N-benzoylphenylalanine and N-benzoylphenylalaninol, asperphenamate, was isolated from solid cultures of Penicillium brevicompactum.Isotope from L-phenylalanine was well incorporated into both benzoyl groups and into the phenylalanine and phenylalaninol moieties.Isotope from benzoic acid was also well incorporated into asperphenamate.Key Word Index-Penicillium brevicompactum; Hyphomycetes; fungus; biosynthesis; asperphenamate; phenylalanine derivatives.

Electrophilic Sulfonium-Promoted Peptide and Protein Amidation in Aqueous Media

Wan, Chuan,Feng, Yuan,Hou, Zhanfeng,Lian, Chenshan,Zhang, Liang,An, Yuhao,Sun, Jinming,Yang, Dongyan,Jiang, Chenran,Yin, Feng,Wang, Rui,Li, Zigang

supporting information, p. 581 - 586 (2022/01/20)

A novel amidation strategy using electrophilic sulfonium, which is soluble and stable in aqueous conditions, was developed. The sulfoniums could activate thioacid and carboxyl acid to efficiently react with amines to afford amides. This method enables applications in amidation in both aqueous media and solid-phase peptide synthesis, peptide/protein modifications, and reactive lysines of a proteome at pH 10 with activity-based protein profiling. A peptide ligand-directed labeling of the USP7-UBL2 domain was also performed using this method.

Identification and validation of selective deubiquitinase inhibitors

Auld, Douglas,Buhrlage, Sara J.,Casalena, Dominick,Chan, Wai Cheung,Dhe-Paganon, Sirano,Hu, Bin,Liu, Xiaoxi,Magin, Robert S.,Marto, Jarrod A.,Roberts, Rebekka M.,Seo, Hyuk-Soo,Varca, Anthony C.,Zhu, He

, p. 1758 - 13,1771 (2021/12/20)

Deubiquitinating enzymes (DUBs) are a class of isopeptidases that regulate ubiquitin dynamics through catalytic cleavage of ubiquitin from protein substrates and ubiquitin precursors. Despite growing interest in DUB biological function and potential as therapeutic targets, few selective small-molecule inhibitors and no approved drugs currently exist. To identify chemical scaffolds targeting specific DUBs and establish a broader framework for future inhibitor development across the gene family, we performed high-throughput screening of a chemically diverse small-molecule library against eight different DUBs, spanning three well-characterized DUB families. Promising hit compounds were validated in a series of counter-screens and orthogonal assays, as well as further assessed for selectivity across expanded panels of DUBs. Through these efforts, we have identified multiple highly selective DUB inhibitors and developed a roadmap for rapidly identifying and validating selective inhibitors of related enzymes.

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives

Ni, Qijian,Wang, Xuyang,Xu, Fangfang,Chen, Xiaoyun,Song, Xiaoxiao

supporting information, p. 3155 - 3158 (2020/03/23)

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

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