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Structure

Fmoc-4-benzoyl-D-phenylalanine

CAS
117666-97-4
Catalog Number
ACM117666974-1
Category
Amino Acids
Molecular Weight
491.5
Molecular Formula
C31H25NO5

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Specification

Description
Fmoc-D-Bpa-OH, or N-[(9-fluorenylmethoxycarbonyl)-2-(4'-borono)phenyl]alanine, is a modified amino acid that has a boron atom and a fluorenylmethoxycarbonyl (Fmoc) group attached to the phenylalanine residue. First synthesized by Sheppard et al. in 1993, Fmoc-D-Bpa-OH has been widely used as a non-natural amino acid in peptide chemistry and as a tool in protein engineering and biophysical studies.
IUPAC Name
(2R)-3-(4-benzoylphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Canonical SMILES
C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
InChI
1S/C31H25NO5/c33-29(21-8-2-1-3-9-21)22-16-14-20(15-17-22)18-28(30(34)35)32-31(36)37-19-27-25-12-6-4-10-23(25)24-11-5-7-13-26(24)27/h1-17,27-28H,18-19H2,(H,32,36)(H,34,35)/t28-/m1/s1
InChI Key
SYOBJKCXNRQOGA-MUUNZHRXSA-N
Boiling Point
729.0±60.0 ℃at 760 mmHg
Flash Point
394.7±32.9 ℃
Density
1.3±0.1 g/cm3
Application
Fmoc-D-Bpa-OH has various potential applications in diverse fields, including peptide chemistry, protein engineering, and biophysical studies. In peptide chemistry, Fmoc-D-Bpa-OH can be used as a non-natural amino acid to introduce chemical diversity into peptide sequences, which can then be used for various applications such as drug design and development. In protein engineering, Fmoc-D-Bpa-OH can be used to introduce non-natural amino acids into proteins, which can then be used to modulate protein activity and stability.
Exact Mass
491.173279
Functional Group
Fmoc
LogP
6.37
MDL Number
MFCD00237666
PSA
92.7
Refractive Index
1.644
Storage Temperature
4 ℃
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine
Vapor Pressure
0.0±2.5 mmHg at 25℃
WGK Germany
3
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