Fmoc-Aib-OH

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Cat Number

INT94744500

CAS Number

94744-50-0

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CAS Number

94744-50-0

EINECS

619-072-5

Storage

2-8℃

Synonyms

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid;N-FMOC-C-ALPHA-METHYLALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-ALPHA-METHYL-L-ALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-ALPHA-AMINOISOBUTYRIC ACID

Molecular Formula

C19H19NO4

Molecular Weight

325.36

Smiles

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

Appearance

White to off-white solid

Melting Point

182-188℃

Boiling Point

544.3℃

Relative Density

1.26

pKa

3.98

General Description

Fmoc-Aib-OH (Fmoc-alpha-aminoisobutyric acid) is an Fmoc-protected version of the non-proteinogenic amino acid Aib. It is characterized by two methyl groups on the alpha-carbon, which induces strong conformational preferences.

Mechanism of Action

It acts as a helix-inducer in peptide synthesis. Due to the Thorpe-Ingold effect of the gem-dimethyl groups, it severely restricts the backbone dihedral angles, strongly promoting the formation of 3(10)-helices or alpha-helices in synthetic peptides.

Application

It is extensively used to stabilize the secondary structure of therapeutic peptides, enhancing their biological activity and resistance to proteolysis in serum.