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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C31H25NO5
CAS Number:
117666-96-3
Molecular Weight:
491.53
UNSPSC Code:
12352209
MDL number:
MFCD00151937

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Product Name

Fmoc-p-Bz-Phe-OH, Fmoc-L-p-benzoylphenylalanine Novabiochem®

SMILES string

N([C@@H](Cc4ccc(cc4)C(=O)c5ccccc5)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3

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

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

Quality Level

200

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

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.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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