Fmoc-4-azidophenylalanine

Catalog Number

ACM163217434-1

Product Name

Fmoc-4-azidophenylalanine

Structure

CAS

163217-43-4

Category

Amino Acids

Description

Fmoc-4-azido-L-phenylalanine is a compound used in peptide synthesis as a non-natural amino acid due to its unique properties. It is an azido derivative of the amino acid phenylalanine, with an Fmoc (fluorenylmethoxycarbonyl) group protecting its amine function. The azido group can react with alkenes or alkynes via Huisgen 1,3-dipolar cycloaddition, also known as click chemistry, to generate stable triazole linkages. This reaction allows for the creation of complex peptide structures with high efficiency and yield.

Synonyms

FMOC-P-AZIDO-L-PHE-OH, Fmoc-L-4-azidophenylalanine, FMOC-PHE(N3)-OH, Fmoc-L-4-azidophe, Fmoc-Phe(4-N3)-OH

IUPAC Name

(2S)-3-(4-azidophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

Molecular Weight

428.4

Molecular Formula

C24H20N4O4

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)N=[N+]=[N-])C(=O)O

InChI

1S/C24H20N4O4/c25-28-27-16-11-9-15(10-12-16)13-22(23(29)30)26-24(31)32-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,31)(H,29,30)/t22-/m0/s1

Application

Fmoc-4-azido-L-phenylalanine is used as a building block in peptide synthesis to create peptides with specific properties and functions. It has been used to create membrane-active peptides, bioconjugates, and enzyme inhibitors, among other things.

Color

Off-white to brownish

Exact Mass

428.148

Form

powder

Functional Group

Fmoc

LogP

5.00646

MDL Number

MFCD00237665

PSA

125.38

Storage Temperature

Store at 0-8 ℃

Type

Unusual Amino Acids, Azide and Alkyne containing Amino Acids

MSDS

COA

Spec Sheet