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931853

Sigma-Aldrich

SPhos Pd G6 acylation

greener alternative

≥95%

Synonym(s):

(SPhos)Pd(4-CH2CH2CONHSPh)Br

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About This Item

Empirical Formula (Hill Notation):
C39H47BrNO6PPd
CAS Number:
2723495-97-2
Molecular Weight:
843.09
MDL number:
MFCD34704619
UNSPSC Code:
12352100
NACRES:
NA.21
Pricing and availability is not currently available.

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

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greener alternative category

Aligned

General description

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Application

SPhos Pd G6 acylation is an oxidative addition complex (OAC) of SPhos for use in bioconjugation. The pendant NHS-functional group allows coupling to protein amines through a selective acylation. The protein-OAC can then be reacted with a second, cysteine-containing protein. This facile approach allows for protein homodimerization as well as the formation of antibody-protein conjugates.

Learn more about G6 Buchwald precatalysts

Other Notes

Palladium–Protein Oxidative Addition Complexes by Amine-Selective Acylation

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Heemal H Dhanjee et al.
Journal of the American Chemical Society, 142(51), 21237-21242 (2020-12-16)
Palladium oxidative addition complexes (OACs) are traditionally accessed by treating an aryl halide-containing substrate with a palladium(0) source. Here, a new strategy to selectively prepare stable OACs from amino groups on native proteins is presented. The approach relies on an
Muhammad Jbara et al.
Angewandte Chemie (International ed. in English), 60(21), 12109-12115 (2021-03-18)
Organometallic reagents enable practical strategies for bioconjugation. Innovations in the design of water-soluble ligands and the enhancement of reaction rates have allowed for chemoselective cross-coupling reactions of peptides and proteins to be carried out in water. There are currently no
Ryan P King et al.
Organic letters, 23(20), 7927-7932 (2021-10-07)
The utilization of isolated Palladium Oxidative Addition Complexes (OACs) has had a significant impact on Pd-catalyzed and Pd-mediated cross-coupling reactions. Despite their importance, widespread utility of OACs has been limited by the instability of their precursor complexes. Herein, we report

Articles

Buchwald G6 Precatalysts: Oxidative Addition Complexes

Buchwald G6 precatalysts are oxidative addition complexes that are thermally, air, and moisture stable. The catalyst activation doesn’t require a base and generates innocuous byproducts.

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