21691-41-8

Basic information

• Product Name: Z-MEALA-OH
• Synonyms: N-ALPHA-CBZ-N-ALPHA-METHYL-L-ALANINE;N-ALPHA-CARBOBENZOXY-N-METHYL-L-ALANINE;N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-L-ALANINE;Z-L-MEALA-OH;Z-MEALA-OH;Z-METHYL-L-ALANINE;Z-N-ME-ALANINE;Z-N-ME-ALA-OH
• CAS NO: 21691-41-8
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• EINECS: 1533716-785-6
• Mol File: 21691-41-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 54-56℃
• Boiling Point: 423 °C at 760 mmHg
• Flash Point: 209.6 °C
• Appearance: /
• Density: 1.222
• Vapor Pressure: 9.16E-07mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 2-8°C
• PKA: 4.01±0.10(Predicted)
• CAS DataBase Reference: Z-MEALA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-MEALA-OH(21691-41-8)
• EPA Substance Registry System: Z-MEALA-OH(21691-41-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 21691-41-8(Hazardous Substances Data)

Usage

General Description

Z-MEALA-OH, also known as Benzyloxycarbonyl-Met-Ala-Leu-Ala-OH, is a chemical compound primarily used in scientific research. It is particularly utilized in the field of biochemistry and molecular biology for peptide synthesis, which is essentially the production of peptides used in drug development and biochemical research. Peptides are chains of amino acids that are combined together in a specific order. Z-MEALA-OH is an important component in this process as its composition directly contributes to peptide synthesis. The "Z" in Z-MEALA-OH refers to a protective group used in peptide synthesis, and "OH" refers to a hydroxyl group, an important functional group in organic chemistry.

InChI:InChI=1/C12H15NO4/c1-9(11(14)15)13(2)12(16)17-8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3,(H,14,15)

Upstream product

• 1142-20-7 N-Cbz-Ala 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 74-88-4 methyl iodide 
• 37661-60-2 phenylmethyl (4S)-5-oxo-4-methyl-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 1403954-14-2 C₃₈H₄₀N₄O₆ 
• 1257235-12-3 4-{2-[2-(benzyloxycarbonyl-methyl-amino)-propionylamino]-3,3-dimethyl-butyryl}-3-(3,4-difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester 
• 1257235-08-7 (1-{1-[6-(3,4-difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester 
• 1257235-00-9 (1-{1-[6-(3,4-difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester 
• 1257234-80-2 4-{2-[2-(benzyloxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester 
• 1257235-49-6 {1-[1-(6-hydroxy-4-isopropylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-2,2-dimethyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid benzyl ester 
• 1257235-33-8 4-{2-[2-(benzyloxycarbonyl-methyl-amino)-propionylamino]-3,3-dimethyl-butyryl}-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester 
• 1257313-25-9 (1-{1-cyclohexyl-2-[4-cyclopropanecarbonyl-6-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic benzyl ester 
• 1218929-74-8 (1-{1-[4-cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester 
• 1218929-60-2 (3aR,6aR)-4-{2[(2S)-(benzyloxycarbonyl-N-methylamino)-propionylamino]-(2S)-cyclohexyl-acetyl}-(3S)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester 
• 1218929-50-0 (3aR,6aR)-4-{2[(2S)-(benzyloxycarbonyl-N-methylamino)-propionylamino]-(2S)-cyclohexyl-acetyl}-(3R)-(1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester 

Relevant articles and documents

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Synthesis of N-alkyl-N-methyl amino acids. Scope and limitations of base-induced N-alkylation of Cbz-amino acids

The reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids with NaH/alkyl iodides gave the corresponding N-Cbz-N-alkyl derivatives in good to high yields. The scope and limitations of this simple N-alkylation reaction were investigated as a convenient and flexible attempt to prepare unsymmetrically N,N-diprotected α-amino acids. The procedure is based on the N-alkylation of N-carbamoyl amino acids, a one-pot deprotection/protection sequence without extensive purification of the products. Protection of the carboxyl function is not required while the starting materials are inexpensive and commercially available.

A simple and rapid protocol for N-methyl-α-amino acids

A two step strategy for optically pure N-Protected-N-methyl-α-amino acids starting from N-protected-α-amino acids via reductive cleavage of oxazolidinones using NaCNBH3/TMSCl is described.