Fmoc-N-methyl-L-isoleucine

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Cat Number

INT138775221

CAS Number

138775-22-1

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Product Detail Description Customer Q&A

CAS Number

138775-22-1

Storage

2-8℃

Synonyms

FMOC-L-MEILE-OH;FMOC-N-ME-ILE-OH

Molecular Formula

C22H25NO4

Molecular Weight

367.44

Smiles

C(O)(=O)[C@H]([C@@H](C)CC)N(C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)C

Appearance

White to off-white solid

Melting Point

177-183℃

Boiling Point

537.3℃

Relative Density

1.19

pKa

3.94

General Description

Fmoc-N-methyl-L-isoleucine is a highly specialized amino acid derivative that combines the bulky, branched side chain of L-isoleucine with an N-methylated peptide backbone, all protected by an Fmoc group.

Mechanism of Action

It acts as a conformational anchor within a peptide sequence. The N-methylation at the isoleucine residue significantly restricts the rotation of the peptide bond and eliminates a hydrogen-bond donor, which is a key strategy for increasing the lipophilicity and membrane permeability of peptides.

Application

It is primarily used in the synthesis of N-methylated cyclic peptides and peptidomimetics designed to cross biological barriers or resist enzymatic degradation.