FMOC-N-Methyl-L-alanine

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Cat Number

INT84000077

CAS Number

84000-07-7

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CAS Number

84000-07-7

EINECS

1533716-785-6

Storage

2-8℃

Synonyms

(9H-Fluoren-9-yl)MethOxy]Carbonyl N-Me-Ala-OH

Molecular Formula

C19H19NO4

Molecular Weight

325.36

Smiles

C[C@@H](C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Appearance

White to off-white solid

Melting Point

150℃

Boiling Point

514.9℃

Relative Density

1.26

pKa

3.92

General Description

FMOC-N-Methyl-L-alanine is the Fmoc-protected form of N-methyl-L-alanine, providing the smallest possible N-methylated amino acid building block for synthetic applications.

Mechanism of Action

It functions as a conformational probe. Despite its small size, the N-methyl group significantly alters the peptide bond's electronic character and steric requirements compared to standard alanine.

Application

It is widely used in the synthesis of cyclic peptides and in the study of peptide folding and protein-protein interaction inhibitors.

Aurilide family of marine cyclodepsipeptides exhibit potent cytotoxicity against various cancer cell lines. A recurring feature in the syntheses of these natural products is the use of Fmoc-N-methyl-L-alanine as a key building block for constructing the pentapeptide domain. For instance, in the total synthesis of aurilide (1), Fmoc-N-methyl-L-alanine was employed to introduce the N-methylated alanine residue at the appropriate position via esterification with the polyketide fragment. Fmoc-N-methyl-L-alanine has strategic importance in enabling the convergent assembly of these complex depsipeptides, facilitating macrocyclization and the late-stage introduction of sensitive heterocycles.

Fig. 1 FMOC-N-Methyl-L-alanine for the synthesis of aurilide 1. (Michon S.; et al. 2021)