35023-55-3

Basic information

• Product Name: H-L-MEALA-OME HCL
• Synonyms: [(2S)-1-methoxy-1-oxo-propan-2-yl]-methyl-azanium chloride;[(2S)-1-methoxy-1-oxopropan-2-yl]-methylazanium chloride;N-Me-L-Ala-OMe HCl;N-Me-L-Ala-OMe;(S)-METHYL 2-(METHYLAMINO)PROPANOATE HCL;H-L-MEALA-OME HCL;N-ME-ALA-OME;N-METHYL-L-ALANINE METHYL ESTER HYDROCHLORIDE
• CAS NO: 35023-55-3
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 153.61
• EINECS: 201-215-5
• Product Categories: GLYCINESCAFFOLD;N-Methyl Amino Acids
• Mol File: 35023-55-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 131.3±23.0 °C(Predicted)
• Appearance: /
• Density: 0.946±0.06 g/cm3(Predicted)
• Storage Temp.: Store at 0°C
• PKA: 7.47±0.10(Predicted)
• CAS DataBase Reference: H-L-MEALA-OME HCL(CAS DataBase Reference)
• NIST Chemistry Reference: H-L-MEALA-OME HCL(35023-55-3)
• EPA Substance Registry System: H-L-MEALA-OME HCL(35023-55-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• Hazardous Substances Data: 35023-55-3(Hazardous Substances Data)

Usage

General Description

H-L-MEALA-OME HCL is a chemical compound that consists of the combination of H-L-MEAL and hydrochloric acid. H-L-MEAL, also known as N-hydroxysuccinimide, is a reagent commonly used in peptide synthesis to activate carboxylic acids for amide bond formation. When it reacts with hydrochloric acid, it forms H-L-MEALA-OME HCL, which is a derivative of H-L-MEAL with improved stability and solubility. H-L-MEALA-OME HCL is also used in the preparation of pharmaceuticals and other organic synthesis applications.

Upstream product

• 67-56-1 methanol 
• 24164-72-5 Z-L-MeAlaOMe 
• 3913-67-5 N-methylalanine 
• 610800-48-1 (S)-methyl 2-(N-methyl-4-nitrobenzenesulfonamido)propanoate 

Downstream Products

• 116871-78-4 Z-Phe-NMeAla-OMe 
• 107114-01-2 N-methyl-N-(phenylthiomethyl)alanine methyl ester 
• 107114-03-4 (2R,3S,4R)-1,2-Dimethyl-4-phenyl-pyrrolidine-2,3-dicarboxylic acid dimethyl ester 
• 107114-02-3 (2R,3R,4S)-1,2-Dimethyl-3-phenyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester 
• 438240-64-3 (S)-2-[((2S,4R)-2-{(S)-3-(1-Benzyl-1H-indol-3-yl)-2-[((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-propionylamino}-4-methyl-octanoyl)-methyl-amino]-propionic acid methyl ester 
• 438240-68-7 C₄₀H₆₇N₅O₁₀ 
• 438240-71-2 (S)-2-[((2S,4R)-2-{(S)-3-(4-Benzyloxy-phenyl)-2-[((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-propionylamino}-4-methyl-octanoyl)-methyl-amino]-propionic acid methyl ester 
• 438240-70-1 (S)-2-({(2S,4R)-2-[(S)-2-[((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-3-(4-methoxy-phenyl)-propionylamino]-4-methyl-octanoyl}-methyl-amino)-propionic acid methyl ester 
• 438240-67-6 (S)-2-[((2S,4R)-2-{(S)-2-[((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-4-phenyl-butyrylamino}-4-methyl-octanoyl)-methyl-amino]-propionic acid methyl ester 
• 438240-69-8 (S)-2-[((2S,4R)-2-{(S)-2-[((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionylamino}-4-methyl-octanoyl)-methyl-amino]-propionic acid methyl ester 
• 438241-23-7 (S)-2-[((S)-2-{(S)-2-[((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionylamino}-octanoyl)-methyl-amino]-propionic acid methyl ester 

Relevant articles and documents

Pithohirolide, an antimicrobial tetradepsipeptide from a fungus Pithomyces chartarum

Pithohirolide (1), a new depsipeptide, was isolated from an ascomycetous fungus Pithomyces chartarum TAMA 581. The planar structure of 1 was elucidated on the basis of NMR and MS analyses and the absolute configuration was determined by the advanced Marfey’s analysis, chiral-phase HPLC analysis, and synthesis of degradation product. Compound 1 possesses a cyclic structure comprising (S)-2-hydroxy-3-phenylpropanoic acid, (S)-3-hydroxy-3-phenylpropanoic acid, (S)-2-hydroxyisovaleric acid, and N-methyl-l-alanine, connected via three ester and one amide linkages. Compound 1 exhibited antimicrobial activity against Staphylococcus aureus and Saccharomyces cerevisiae at MIC 3.1 μg ml?1.

Deprotectlon of N-Nosyl-α-amlno acids by using solid-supported mercaptoacetic acid

A simple and efficient synthesis of a solid-supported thiol has been developed. Mercaptoacetic acid was first protected by the dimethoxytrityl group and then anchored to Wang resin through an ester bond. Deprotection of the thiol function led to resin-supported mercaptoacetic acid, a useful supported thiol reagent that can be used in the polymer-assisted solution-phase removal of nosyl (Ns) groups from the amino function of a-amino acids in peptide synthesis.

Synthesis and use of 2H-azirin-3-amines as dipeptide synthons

The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx=alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.