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
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.
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine
Vapor Pressure
0.0±2.5 mmHg at 25℃