Structure

Fmoc-2-cyano-L-phenylalanine

CAS
401933-16-2
Catalog Number
ACM401933162
Category
Amino Acids
Molecular Weight
412.4
Molecular Formula
C25H20N2O4

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Specification

Description
Fmoc-2-cyano-L-phenylalanine (Fmoc-Cy-OR) is a protected derivative of L-phenylalanine, which is widely used in the field of peptide synthesis. Fmoc-Cy-OR is a relatively new amino acid (AA) that has been introduced in the field of solid-phase peptide synthesis (SPPS). Fmoc stands for the 9-fluorenylmethyloxycarbonyl, which is a protecting group used to protect the α-amino group of the AA during SPPS. This protects the AA from reaction with other reagents when amino acids are coupled in peptide synthesis reactions.
Synonyms
Fmoc-D-2-cyanophenylalanine, 2-Cyano-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-cyanophenyl)propanoic acid, Fmoc-2-cyano-L-phenylalanine, Fmoc-L-2-Cyanophenylalanine, Fmoc-Phe(2-CN)-OH
IUPAC Name
(2S)-3-(2-cyanophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Canonical SMILES
C1=CC=C(C(=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C#N
InChI
1S/C25H20N2O4/c26-14-17-8-2-1-7-16(17)13-23(24(28)29)27-25(30)31-15-22-20-11-5-3-9-18(20)19-10-4-6-12-21(19)22/h1-12,22-23H,13,15H2,(H,27,30)(H,28,29)/t23-/m0/s1
InChI Key
ACFGBBASKOIPEW-QHCPKHFHSA-N
Boiling Point
666.0±55.0 ℃at 760 mmHg
Flash Point
356.6±31.5 ℃
Density
1.4±0.1 g/cm3
Application
Fmoc-Cy-OR is widely used in the field of peptide synthesis, specifically in the construction of peptidomimetics due to its structural similarities to various natural peptides.
Exact Mass
412.142303
Functional Group
Fmoc
LogP
4.84
MDL Number
MFCD01863771
PSA
99.42
Refractive Index
1.672
Storage Temperature
4 ℃
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine
Vapor Pressure
0.0±2.1 mmHg at 25℃
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