56564-52-4

Basic information

• Product Name: H-D-MEPHE-OH HCL
• Synonyms: H-D-MEPHE-OH HCL;N-ME-D-PHE-OH HCL;N-METHYL-D-PHENYLALANINE HYDROCHLORIDE;N-ALPHA-METHYL-D-PHENYLALANINE HYDROCHLORIDE;N-Me-D-Phe-OMe·HCl;N-Me-D-Phe-OMe.;(R)-2-(MethylaMino)-3-phenylpropanoic acid;N-Methyl-D-phenylalanine HCl
• CAS NO: 56564-52-4
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 215.68
• Product Categories: amino acids
• Mol File: 56564-52-4.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 308.3 °C at 760 mmHg
• Flash Point: 140.3 °C
• Appearance: /Solid
• Density: 1.126
• Vapor Pressure: 0.000297mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: −20°C
• CAS DataBase Reference: H-D-MEPHE-OH HCL(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-MEPHE-OH HCL(56564-52-4)
• EPA Substance Registry System: H-D-MEPHE-OH HCL(56564-52-4)

Safety Data

• Hazardous Substances Data: 56564-52-4(Hazardous Substances Data)

Usage

Uses

N-alpha-Methyl-D-phenylalanine is used for preparation of phosphate/sulfate ester compounds and their pharmaceutical composition for inhibition of protein interacting NIMA (PIN 1).

InChI:InChI=1/C10H13NO2/c1-11-9(10(12)13)7-8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3,(H,12,13)/t9-/m1/s1

Upstream product

• 7474-06-8 (S)-2-chloro-3-phenyl-propionic acid 
• 74-89-5 methylamine 
• 93473-37-1 (S)-2-(Dimethylamino-methyleneamino)-3-phenyl-propionic acid methyl ester 
• 77-78-1 dimethyl sulfate 
• 2566-35-0 N-methylphenylalanine 
• 1108702-38-0 N-benzyl,N-methyl-D-phenylalanine 
• 1187551-28-5 grassystatin A 
• 1187551-30-9 grassystatin C 
• 1255709-51-3 7,39-epi-Lagunamide A 
• 1255709-52-4 lagunamide B 
• 37553-65-4 N-tert-butoxycarbonyl-N-methyl-D-phenylalanine 
• 93529-74-9 (S)-N-(4-chlorobenzylidene)phenylalanine methyl ester 
• 1572177-03-7 tasiamide E 
• 1572177-01-5 tasiamide C 

Downstream Products

• 130008-09-2 methyl N-methyl-D-phenylalaninate hydrochloride 
• 1571105-51-5 C₆₀H₉₄N₁₂O₁₀ 
• 1571105-54-8 C₅₈H₉₀N₁₂O₁₀ 
• 1571105-48-0 C₆₁H₉₄N₁₂O₁₀ 
• 138775-05-0 (2R)-2-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methylamino)-3-phenyl-propionic acid 
• 194736-83-9 D-N-Me-Phe-FDAA 
• 1309656-45-8 C₂₀H₂₇N₂O₄P 
• 102339-81-1 (2R)-2-(Methylamino)-3-phenylpropan-1-ol 

Relevant articles and documents

Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium Caldora penicillata

Hoshinoamide C (1), an antiparasitic lipopeptide, was isolated from the marine cyanobacterium Caldora penicillata. Its planar structure was elucidated by spectral analyses, mainly 2D NMR, and the absolute configurations of the α-amino acid moieties were determined by degradation reactions followed by chiral-phase HPLC analyses. To clarify the absolute configuration of an unusual amino acid moiety, we synthesized two possible diastereomers of hoshinoamide C and determined its absolute configuration based on a comparison of their spectroscopic data with those of the natural compound. Hoshinoamide C (1) did not exhibit any cytotoxicity against HeLa or HL60 cells at 10 μM, but inhibited the growth of the parasites responsible for malaria (IC50 0.96 μM) and African sleeping sickness (IC50 2.9 μM).

Isolation, structure elucidation and biological evaluation of lagunamide D: A new cytotoxic macrocyclic depsipeptide from marine cyanobacteria

Lagunamide D, a new cytotoxic macrocyclic depsipeptide, was discovered from a collection of marine cyanobacteria from Loggerhead Key in the Dry Tortugas, Florida. An intramolecular ester exchange was observed, where the 26-membered macrocycle could contract to a 24-membered compound via acyl migration at the 1,3-diol unit, and the transformation product was named lagunamide D'. The planar structures of both compounds were elucidated using a combination of nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectroscopy (HRMS). The absolute configurations were determined on the basis of enantioselective analysis, modified Mosher's analysis, Kishi NMR database, and direct comparison with lagunamide A, a structure closely resembling lagunamide D. Lagunamides A and D displayed low-nanomolar antiproliferative activity against A549 human lung adenocarcinoma cells, while the structural transformation from the 26-membered lagunamide D macrocycle to the 24-membered ring structure for lagunamide D' led to a 9.6-fold decrease in activity. Lagunamide D also displayed potent activity in triggering apoptosis in a dose- and time-dependent manner. Further investigation on the mechanism of action of the lagunamide scaffold is needed to fully explore its therapeutic potential as an anticancer agent.

Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC50value of 26.3?nM.