Specification
Description
Fmoc-p-Bz-Phe-OH is a useful tool for preparing photoactivatable peptide-based affinity probes. On photolysis at 366 nm, Benzoylphenylalanine (Bpa) generates a biradical that has a preference for insertion into C-H bonds, particularly those of Leu, Val and Met side chains. The derivative can be introduced using standard coupling method such as PyBOP and is stable to conditions used in peptide chain extension. For the cleavage of Bpa containing peptide from the resin, the use of thiols and silanes should be avoided as dithioketal formation and reduction, respectively, have been observed.
Synonyms
Fmoc-4-benzoyl-L-phenylalanine
Canonical SMILES
OC(=O)[C@H](Cc1ccc(cc1)C(=O)c2ccccc2)NC(=O)OCC3c4ccccc4-c5ccccc35
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-/m0/s1
InChI Key
SYOBJKCXNRQOGA-NDEPHWFRSA-N
Application
Peptide synthesis.
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine