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4-Benzoylbenzoic acid N-succinimidyl ester

Name: 4-Benzoylbenzoic acid <I>N</I>-succinimidyl ester
Brand: ALDRICH

97%

Synonym(s):

4-Benzoylbenzoic acid, succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₃NO₅

CAS Number:

91990-88-4

Molecular Weight:

323.30

MDL number:

MFCD00058572

UNSPSC Code:

12352200

PubChem Substance ID:

329767795

Assay

97%

form

solid

mol wt

323.3

reaction suitability

reagent type: cross-linking reagent

mp

207-212 °C

storage temp.

−20°C

SMILES string

O=C1CCC(=O)N1OC(=O)c2ccc(cc2)C(=O)c3ccccc3

InChI

1S/C18H13NO5/c20-15-10-11-16(21)19(15)24-18(23)14-8-6-13(7-9-14)17(22)12-4-2-1-3-5-12/h1-9H,10-11H2

InChI key

MVQNJLJLEGZFGP-UHFFFAOYSA-N

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Application

Heterobifunctional photoreactive crosslinker. Succinimidyl ester will react with amines and the benzophenone will react non-specifically upon photoirradiation at approximately 360 nm.

A benzophenone-based photoreactive reagent shown to be useful for synthesizing photoreactive peptides and oligonucleotides.

Pictograms

GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273

Hazard Classifications

Aquatic Acute 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Synthesis and evaluation of an N-acylated photoactivatable analogue of glutathione as probe for glutathione-utilizing enzymes.

Dan Bernardi et al.

Bioorganic & medicinal chemistry letters, 16(6), 1601-1604 (2006-01-03)

The first synthesis of an N-acylated photoactivatable analogue of reduced glutathione is described. N-(4-Benzoylbenzoyl)glutathione (8) was found to be an inhibitor and a photoaffinity probe of purified rat liver glutathione S-transferases.

Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA).

Horacio F Olivo et al.

Bioorganic & medicinal chemistry letters, 20(3), 1153-1155 (2009-12-25)

We have synthesized an analog of dehydroepiandrosterone (DHEA, 1) containing both a benzophenone (BP) and a biotin (Bt) group (DHEA-BP-Bt, 8). Compound 8 was prepared by functionalization on C-17 of 1. Biocytin was reacted with 4-benzoylbenzoic acid and the product

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