38017-89-9

Basic information

• Product Name: L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester
• CAS NO: 38017-89-9
• Molecular Formula: C20H28N2O5
• Molecular Weight: 376.453
• Mol File: 38017-89-9.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester(38017-89-9)
• EPA Substance Registry System: L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester(38017-89-9)

Safety Data

• Hazardous Substances Data: 38017-89-9(Hazardous Substances Data)

Usage

General Description

L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester is a chemical compound that consists of proline and phenylalanine, with a methyl ester group attached. L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester is commonly used as a reagent in organic synthesis and biochemical research. It is also utilized in the production of peptides and proteins, as well as in pharmaceuticals. L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-, methyl ester is known for its stability and its ability to protect peptides from degradation. It is also used as a building block for the synthesis of various pharmaceutical and biologically active compounds.

Upstream product

• 2133-40-6 L-proline methyl ester monohydrochloride 
• 3674-06-4 Boc-Phe-ONSu 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 

Downstream Products

• 70462-58-7 benzyl (tert-butoxycarbonyl)-L-phenylalanyl-L-prolinate 
• 118447-06-6 BOCPheΨProOMe 
• 69936-03-4 (1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate 
• 83825-04-1 L-phenylalanine-L-proline methyl ester 
• 23420-32-8 N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 
• 5654-85-3 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 914771-44-1 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine 

Relevant articles and documents

Synthesis of Cyclic Peptidomimetics via a Pd-Catalyzed Macroamination Reaction

A new method to access cyclic peptidomimetics via a Pd-catalyzed macroamination reaction is presented. Natural amino acid amines are revealed as proficient coupling partners in these transformations. With a commercially available CPhos G3 catalyst system and substrates bearing diverse amino acid and aryl halide backbones, the unique head to side-chain (or side-chain mimic) macrocycles are afforded with ring sizes from 11 to 23 members in yields up to 84%.

Unambiguous stereochemical assignment of cyclo(Phe-pro), cyclo(leu-pro), and cyclo(val-pro) by electronic circular dichroic spectroscopy

2,5-diketopiperazines (DKPs) are cyclic dipeptides ubiquitously found in nature. In particular, cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) are frequently detected in many microbial cultures. Each of these DKPs has four possible stereoisomers due to the presence of two chirality centers. However, absolute configurations of natural DKPs are often ambiguous due to the lack of a simple, sensitive, and reproducible method for stereochemical assignment. This is an important problem because stereochemistry is a key determinant of biological activity. Here, we report a synthetic DKP library containing all stereoisomers of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro). The library was subjected to spectroscopic characterization using mass spectrometry, NMR, and electronic circular dichroism (ECD). It turned out that ECD can clearly differentiate DKP stereoisomers. Thus, our ECD dataset can serve as a reference for unambiguous stereochemical assignment of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) samples from natural sources. The DKP library was also subjected to a biological screening using assays for E. coli growth and biofilm formation, which revealed distinct biological effects of cyclo(D-Phe-L-Pro).

Chemical profiling of HIV-1 capsid-targeting antiviral PF74

The capsid protein (CA) of HIV-1 plays essential roles in multiple steps of the viral replication cycle by assembling into functional capsid core, controlling the kinetics of uncoating and nuclear entry, and interacting with various host factors. Targetin

Synthesis of 3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione [cyclo(Pro-Phe)] was synthesized by cyclization of prolylphenylalanine and phenylalanylproline methyl esters which were prepared from the corresponding Boc-protected amino acids.