Structure

Fmoc-Bpa-OH

CAS
117666-96-3
Catalog Number
ACM117666963
Category
Amino Acids
Molecular Weight
491.53
Molecular Formula
C31H25NO5

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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.
Assay
≥98.0%
Beilstein
7672022
Color
white
Form
powder
Functional Group
Fmoc
MDL Number
MFCD00151937
NACRES
NA.26
PubChem ID
329748821
Quality Level
100
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Storage Temperature
2-8℃
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine
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