Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester, CAS No. 152548-66-8

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152548-66-8

Catalog No. EBD42226

CAS 152548-66-8

Name Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester

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Basic Information

Synonyms: (2S)-4-tert-butoxy-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}-4-oxobutanoicacid(non-preferredname) Fmoc-N-methyl-L-asparticacid4-tert-butylester n-alpha-fmoc-n-alpha-methyl-l-asparticacidbeta-t-butylester n-alpha-(9-fluorenylmethoxycarbonyl)-n-alpha-methyl-l-asparticacidbeta-tbutylester n-alpha-(9-fluorenylmethyloxycarbonyl)-n-alpha-methyl-l-asparticacidbeta-tert-butylester fmoc-l-measp(tbu)-oh fmoc-measp(otbu)-oh fmoc-n-me-asparticacid(otbu)-oh fmoc-n-methyl-l-asparticacidbeta-t-butylester N-(9-Fluorenylmethyloxycarbonyl)-N-methyl-L-asparticacid4-tert-butylester Fmoc-N-Me-Asp(OtBu)-OH

Molecular Formula: C24H27NO6

Molecular Weight: 425.47

MDL Number: MFCD00237027

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester is a protected, N-methylated derivative of aspartic acid. It features an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group and a side-chain carboxylic acid protected as a tert-butyl ester. This specific protection scheme (Fmoc on the α-amine, tert-butyl on the β-carboxyl) makes it a crucial building block for solid-phase peptide synthesis (SPPS) using the standard Fmoc/t-Bu strategy. Its primary application is in the synthesis of peptides containing N-methylated amino acid residues, particularly N-methyl-aspartate. N-methylation is a key modification in medicinal chemistry and peptide drug discovery, as it can enhance metabolic stability, improve membrane permeability, alter conformational properties, and reduce the potential for hydrogen bonding, thereby modulating the peptide's biological activity and pharmacokinetic profile. This compound is specifically designed to be incorporated into peptide chains during automated or manual SPPS. As a specialized, protected amino acid derivative, it is a fundamental reagent in peptide research and the development of peptide-based therapeutics, diagnostics, and biochemical tools. It is not a commodity chemical but a high-value, research-grade building block.

Physical Properties

Melting Point: 135-140 °C

Boiling Point: 598.7 °C at 760 mmHg

Flash Point: 315.9 °C

Density: 1.237 g/cm3

Storage: 2-8°C

Safety Information

Packing Level: III

Hazard Category: 9

Transport Codes: 3077

Analytical Data

Appearance: white to off-white crystalline powder