35023-55-3

Usage

Uses

Used in Pharmaceutical Preparation:
H-L-MEALA-OME HCL is used as a reagent in the pharmaceutical industry for the synthesis of various drugs. Its improved stability and solubility compared to H-L-MEAL make it a preferred choice for facilitating the formation of amide bonds in the synthesis process.
Used in Organic Synthesis:
In the field of organic synthesis, H-L-MEALA-OME HCL is utilized as a versatile reagent for the activation of carboxylic acids. This activation is essential for the formation of amide bonds, which are crucial in the synthesis of various organic compounds.
Used in Peptide Synthesis:
H-L-MEALA-OME HCL is used as an activating agent in peptide synthesis. Its ability to activate carboxylic acids allows for the efficient formation of amide bonds, which are the backbone of peptide chains. This makes it an essential component in the synthesis of peptides and proteins for research and therapeutic applications.

Upstream product

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

Downstream Products

• 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 
• 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 
• 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 
• 438240-70-1 (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 
• 438240-71-2 (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 
• 438240-68-7 C₄₀H₆₇N₅O₁₀ 
• 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 
• 107114-02-3 (2R,3R,4S)-1,2-Dimethyl-3-phenyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester 
• 107114-03-4 (2R,3S,4R)-1,2-Dimethyl-4-phenyl-pyrrolidine-2,3-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

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.

Lewis acid catalysed methylation of N-(9H-fluoren-9-yl)methanesulfonyl (Fms) protected lipophilic α-amino acid methyl esters

This work reports an efficient Lewis acid catalysed N-methylation procedure of lipophilic α-amino acid methyl esters in solution phase. The developed methodology involves the use of the reagent system AlCl3/diazomethane as methylating agent and α-amino acid methyl esters protected on the amino function with the (9H-fluoren-9-yl)methanesulfonyl (Fms) group. The removal of Fms protecting group is achieved under the same conditions to those used for Fmoc removal. Thus the Fms group can be interchangeable with the Fmoc group in the synthesis of N-methylated peptides using standard Fmoc-based strategies. Finally, the absence of racemization during the methylation reaction and the removal of Fms group were demonstrated by synthesising a pair of diastereomeric dipeptides.

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.

"One-pot" methylation of N-nosyl-α-amino acid methyl esters with diazomethane and their coupling to prepare N-methyl dipeptides

N-Nosyl-α-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoe amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by 1H NMR and HPLC.

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.