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8.52287

Sigma-Aldrich

Fmoc-p-Bz-Phe-OH

Fmoc-L-p-benzoylphenylalanine Novabiochem®

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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

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

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

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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