(2R,5S,8S,11S,15S)-5-[3-({(E)-amino[(methylcarbamoyl)amino]methylidene}amino)propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid

Base Information

• Chemical Name: (2R,5S,8S,11S,15S)-5-[3-({(E)-amino[(methylcarbamoyl)amino]methylidene}amino)propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid
• CAS No.: 243975-37-3
• Molecular Formula: C₂₉H₄₁N₉O₁₀
• Molecular Weight: 675.699
• Mol file: 243975-37-3.mol

Synonyms:Argifin;FTD 0668

Chemical Property of (2R,5S,8S,11S,15S)-5-[3-({(E)-amino[(methylcarbamoyl)amino]methylidene}amino)propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid

Chemical Property:

• PSA: 305.77000
• Density: 1.49g/cm³
• LogP: -0.66080

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Argifin (also known as FTD 0668) is a cyclic pentapeptide natural product that acts as a potent chitinase inhibitor, with its binding affinity largely dependent on the Arg(MC)-MePhe dipeptide motif. Its structure features a complex macrocyclic scaffold with multiple amide bonds, a benzyl group, and dicarboxylic acid moieties, which contribute to its inhibitory activity. (2R,5S,8S,11S,15S)-5-[3-({(E)-amino[(methylcarbamoyl)amino]methylidene}amino)propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid has been synthesized via an efficient solid-phase method, avoiding problematic side reactions like aspartimide formation, and its structure-activity relationships highlight its potential as a lead for developing chitinase-targeting therapeutics.

Technology Process of (2R,5S,8S,11S,15S)-5-[3-({(E)-amino[(methylcarbamoyl)amino]methylidene}amino)propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid

There total 9 articles about (2R,5S,8S,11S,15S)-5-[3-({(E)-amino[(methylcarbamoyl)amino]methylidene}amino)propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11,15-dicarboxylic acid 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: 68.0%

C99H171N9O15 → cyclo(Nw-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl) (243975-37-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2011.05.073

Reference yield: 65.0%

(2R,5S,8S,11S,15S)-8-Benzyl-5-(3-guanidino-propyl)-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaaza-cycloheptadecane-11,15-dicarboxylic acid (868840-76-0) + 2,5-dioxopyrrolidin-1-yl methylcarbamate (18342-66-0) → cyclo(Nw-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl) (243975-37-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

DOI:10.1016/j.bmcl.2005.07.068

Reference yield: 36.0%

C107H179N9O16 (1324007-50-2) → C37H49N9O11 + cyclo(Nw-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl) (243975-37-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2011.05.073

upstream raw materials:

(2R,5S,8S,11S,15S)-8-Benzyl-5-(3-guanidino-propyl)-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaaza-cycloheptadecane-11,15-dicarboxylic acid

2,5-dioxopyrrolidin-1-yl methylcarbamate

C₄₉H₇₂N₈O₁₂S

C₄₉H₇₄N₈O₁₃S

Refernces

Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold

10.1039/b815077j

The research focuses on the development of an efficient all-solid-phase synthesis method for argifin, a natural product cyclic pentapeptide chitinase inhibitor. The purpose of this study was to improve the synthesis process, overcome side reactions, and provide valuable structure-activity relationship (SAR) data for the argifin scaffold. The researchers successfully developed a new synthesis approach that avoids aspartimide formation during deprotection, using a novel aqueous acidolysis procedure. They also synthesized a series of argifin analogues based on the X-ray structure of argifin in complex with a representative family 18 chitinase, which highlighted the key role of the Arg(MC)-MePhe dipeptide in binding. The chemicals used in the process included Fmoc-protected amino acids, PyBOP/DIPEA for peptide coupling, Pd(Ph3P)4/PhSiH3 for allyl ester cleavage, and various reagents for side-chain manipulation and deprotection, such as 1H-pyrazole-1-carboxamidine hydrochloride and N-succinimidyl N-methylcarbamate. The conclusions drawn from the study emphasized the efficiency of the all-solid-phase route to argifin and its potential for automation and scale-up, as well as the importance of specific residues in the binding affinity of chitinase inhibitors.