272123-01-0

Basic information

• Product Name: N-Butadecanoyl-D-phenylalanine
• Synonyms: N-Butadecanoyl-D-phenylalanine
• CAS NO: 272123-01-0
• Molecular Formula: C23H37NO3
• Molecular Weight: 375.54478
• Mol File: 272123-01-0.mol

Chemical Properties

• Boiling Point: 559.9°Cat760mmHg
• Flash Point: 292.4°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 2.25E-13mmHg at 25°C
• Refractive Index: 1.507
• PKA: 3.63±0.10(Predicted)
• CAS DataBase Reference: N-Butadecanoyl-D-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Butadecanoyl-D-phenylalanine(272123-01-0)
• EPA Substance Registry System: N-Butadecanoyl-D-phenylalanine(272123-01-0)

Safety Data

• Hazardous Substances Data: 272123-01-0(Hazardous Substances Data)

Usage

Uses

suzuki reaction

InChI:InChI=1/C23H37NO3/c1-2-3-4-5-6-7-8-9-10-11-15-18-22(25)24-21(23(26)27)19-20-16-13-12-14-17-20/h12-14,16-17,21H,2-11,15,18-19H2,1H3,(H,24,25)(H,26,27)/t21-/m1/s1

Upstream product

• 63-91-2 L-phenylalanine 
• 544-63-8 n-tetradecanoic acid 
• 112-64-1 tetradecanoyl chloride 
• 1381801-48-4 CH₃(CH₂)12CONHCH(CH₂Ph)COOMe 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 69888-86-4 N-succinimidyl myristate 
• 673-06-3 D-(R)-phenylalanine 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 1027267-20-4 (S)-2-(dodecylamino)-3-phenylpropan-1-ol 
• 1569831-44-2 (S)-4-benzyl-3-decyl-1,2,3-oxathiazolidine 2,2-dioxide 
• 1569830-68-7 (S)-3-(2-(dodecylamino)-3-phenylpropyl)-1-methyl-1H-imidazol-3-ium chloride 
• 1569830-86-9 (S)-3-(2-(tetradecylamino)-3-phenylpropyl)-1-methyl-1H-imidazol-3-ium chloride 
• 1569830-72-3 (S)-3-(2-(nonylamino)-3-phenylpropyl)-1-methyl-1H-imidazol-3-ium chloride 
• 1569831-60-2 (S)-4-benzyl-3-tetradecyl-1,2,3-oxathiazolidine 2,2-dioxide 
• 1569831-53-3 (S)-4-benzyl-3-decyl-1,2,3-oxathiazolidine 2,2-dioxide 
• 1569831-47-5 (S)-4-benzyl-3-nonyl-1,2,3-oxathiazolidine 2,2-dioxide 

Relevant articles and documents

Cyclohexyl-octahydro-pyrrolo[1,2-a]pyrazine-Based Inhibitors of Human N-Myristoyltransferase-1

N-Myristoyltransferase (NMT) is an emerging therapeutic target that catalyzes the attachment of myristate to the N terminus of an acceptor protein. We have developed a medium-throughput assay for screening potential small molecule inhibitors of human NMT-1 consisting of recombinant enzyme, biotinylated peptide substrate, and [3H]myristoyl-CoA. Approximately 16,000 diverse compounds have been evaluated, and significant inhibition of NMT was found with 0.8% of the compounds. From these hits, we have identified the cyclohexyl-octahydro-pyrrolo[1,2-a]pyrazine (COPP) chemotype as inhibitory toward human NMT-1. Thirty-two compounds containing this substructure inhibited NMT-1, with IC50 values ranging from 6 μM to millimolar concentrations, and a quantitative structure-activity relationship equation (r2 = 0.72) was derived for the series. The most potent inhibitor (24, containing 9-ethyl-9H-carbazole) demonstrated competitive inhibition for the peptide-binding site of NMT-1 and noncompetitive inhibition for the myristoyl-CoA site. Computational docking studies using the crystal structure of the highly homologous yeast NMT confirmed that 24 binds with excellent complementarity to the peptide-binding site of the enzyme. To evaluate the ability of 24 to inhibit NMT activity in intact cells, monkey CV-1 cells expressing an N-myristoylated green fluorescent protein (GFP) fusion protein were treated with a known NMT inhibitor or with 24. Each compound caused the redistribution of GFP from the plasma membrane to the cytosol. Furthermore, 24 inhibits cancer cell proliferation at doses similar to those that inhibit protein myristoylation. Overall, these studies establish an efficient assay for screening for inhibitors of human NMT and identify a novel family of inhibitors that compete at the peptide-binding site and have activity in intact cells.

Enzyme entrapment in amphiphilic myristyl-phenylalanine hydrogels

Supramolecular amino acid and peptide hydrogels are functional materials with a wide range of applications, however, their ability to serve as matrices for enzyme entrapment have been rarely explored. Two amino acid conjugates were synthesized and explore

Translation of Mycobacterium Survival Strategy to Develop a Lipo-peptide based Fusion Inhibitor**

The entry of enveloped virus requires the fusion of viral and host cell membranes. An effective fusion inhibitor aiming at impeding such membrane fusion may emerge as a broad-spectrum antiviral agent against a wide range of viral infections. Mycobacterium survives inside the phagosome by inhibiting phagosome–lysosome fusion with the help of a coat protein coronin 1. Structural analysis of coronin 1 and other WD40-repeat protein suggest that the trp-asp (WD) sequence is placed at distorted β-meander motif (more exposed) in coronin 1. The unique structural feature of coronin 1 was explored to identify a simple lipo-peptide sequence (myr-WD), which effectively inhibits membrane fusion by modulating the interfacial order, water penetration, and surface potential. The mycobacterium inspired lipo-dipeptide was successfully tested to combat type 1 influenza virus (H1N1) and murine coronavirus infections as a potential broad-spectrum antiviral agent.

A tripeptide-based self-shrinking hydrogel for waste-water treatment: Removal of toxic organic dyes and lead (Pb2+) ions

A triphenylalanine-based superhydrogel shows automatic syneresis (self-compressing properties) with time and this self-shrinking behavior has been successfully utilized to remove toxic lead ions and organic dyes from waste-water efficiently with the abili

General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis

A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.

A modular approach towards drug delivery vehicles using oxanorbornane-based non-ionic amphiphiles

The self-assembly of non-ionic amphiphiles with a hydroxylated oxanorbornane head-group was controlled using amino acid units as spacers between hydrophilic and lipophilic domains to get spherical supramolecular aggregates. The ability of these systems to harbour therapeutic agents like ibuprofen, and their drug-release profiles were evaluated. Apart from directing the assembly, the intervening amino acid unit was found to help in drug entrapment as well. The presence of cholesterol improved their drug-loading ability, and an encapsulation efficiency of up to 66% was shown by the formulation containing the phenylalanine residue as the spacer (NC1c). There was no burst release, and 45% drug release was observed at the end of 24 h in this case (cf. soyaphosphatidylcholine based formulation = 49%). The results from SEM, Cryo-TEM, PXRD and confocal microscopic studies with some insights into molecular packing in this class of aggregates are also included.

Structure-activity relationship study of syringolin A as a potential anticancer agent

A detailed structure-activity relationship of syringolin A (1), which is a promising antitumor natural product, was described. We previously developed syringolin A analog 2 as a potent proteasome inhibitor by the structure-based drug design of syringolin A. In this Letter, we synthesized a range of analogs of 2, having a different length of the lipophilic chain and substituted aryl group, and their cytotoxicity against human cancer cells was evaluated. It turned out that these modifications greatly affected the cytotoxicity. Further optimization would lead to develop a novel proteasome inhibitor.

Use of N-myristoyl-(S)-phenylalanine for the treatment of diseases involving myristoylation

The invention relates to the use of N-myristoyl-(S)-phenylalanine in the treatment of diseases involving myristoylation such as cancer or AIDS. Medicinal products including N-myristoyl-(S)-phenylalanine which are effective for such purpose.