8.52287

Fmoc-p-Bz-Phe-OH

Fmoc-L-p-benzoylphenylalanine Novabiochem^®

• Synonym(s): Fmoc-p-Bz-Phe-OH, (S)-3-(4-Benzoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid,4-Benzoyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]phenylalanine
• Empirical Formula (Hill Notation): C₃₁H₂₅NO₅
• CAS Number: 117666-96-3
• Molecular Weight: 491.53
• MDL number: MFCD00151937
• UNSPSC Code: 12352209

Properties

• Quality Level: 200
• product line: Novabiochem^®
• Assay: ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: Fmoc
• storage temp.: 2-8°C
• 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

Description

General description

Fmoc-p-Bz-Phe-OH-OH is a useful tool for preparing photoactivatable peptide-based affinity probes ^[1]. 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.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] K. T. O′Neil, et al. (1989) J. Biol. Chem., 264.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Optical rotation α 25/D (c=1 in DMF): -31.0 - -27.0 °
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable