Polyfluorophenyl Ester-Terminated Homobifunctional Cross-Linkers for Protein Conjugation

Wang, Jian; Zhang, Ruyan; Wang, Yacong; Chen, Xiang-Zhao; Yin, Xuguang; Du, Jingjing; Lei, Ze; Xin, Ling-Ming; Gao, Xiang; Liu, Zheng; Guo, Jun

doi:10.1055/s-0036-1590974

Cited by 7 publications

(2 citation statements)

References 12 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phenyl-based esters compose an important class of bioconjugation reagents and are extensively employed in biochemistry and materials science [4,92,93]. These include p-nitrophenyl and fluorinated esters.…”

Section: Phenyl and N-hydroxysuccinimide Estersmentioning

confidence: 99%

“…The trend within the fluorinated phenyl esters is for increasing fluorination to favor reaction thermodynamics, with the tetrafluoro-and pentafluorophenyl esters having comparable free energies of reactions with methylamine to those of the p-nitrophenyl leaving group. Reactions of phenyl [96][97][98][99][100], p-nitrophenyl [84,93,98,101], and fluorophenyl esters [92,93] have been studied experimentally and computationally with various nucleophiles and solvents, with a focus on the transition state structures. For example, a theoretical study of the aminolysis of para-substituted phenyl acetates in vacuo and in acetonitrile was undertaken at the B3LYP/6-31+G(d,p) level of theory, and for the reaction of phenyl acetate with ammonia, a reaction energy (∆E) of −13.09 kcal/mol (−54.77 kJ/mol) was computed.…”

Section: Phenyl and N-hydroxysuccinimide Estersmentioning

confidence: 99%

See 1 more Smart Citation

Thermodynamic Overview of Bioconjugation Reactions Pertinent to Lysine and Cysteine Peptide and Protein Residues

Lopandic,

Merza,

Honek

2023

Compounds

View full text Add to dashboard Cite

Bioconjugation reactions are critical to the modification of peptides and proteins, permitting the introduction of biophysical probes onto proteins as well as drugs for use in antibody-targeted medicines. A diverse set of chemical reagents can be employed in these circumstances to covalently label protein side chains, such as the amine moiety in the side chain of lysine and the thiol functionality in cysteine residues, two of the more frequently employed sites for modification. To provide researchers with a thermodynamic survey of the reaction of these residues with frequently employed chemical modification reagents as well as reactive cellular intermediates also known to modify proteins non-enzymatically, a theoretical investigation of the overall thermodynamics of models of these reactions was undertaken at the T1 and G3(MP2) thermochemical recipe levels (gas phase), the M06-2X/6-311+G(2df,2p)/B3LYP/6-31G(d) (gas and water phase), and the M06-2X/cc-PVTZ(-f)++ density functional levels of theory (water phase). Discussions of the relationship between the reagent structure and the overall thermodynamics of amine or thiol modification are presented. Of additional interest are the observations that routine cellular intermediates such as certain thioesters, acyl phosphates, and acetyl-L-carnitine can contribute to non-enzymatic protein modifications. These reactions and representative click chemistry reactions were also investigated. The computational survey presented herein (>320 reaction computations were undertaken) should serve as a valuable resource for researchers undertaking protein bioconjugation. A concluding section addresses the ability of computation to provide predictions as to the potential for protein modification by new chemical entities, with a cautionary note on protein modification side reactions that may occur when employing synthetic substrates to measure enzyme kinetic activities.

show abstract

Section: Phenyl and N-hydroxysuccinimide Estersmentioning

confidence: 99%

Section: Phenyl and N-hydroxysuccinimide Estersmentioning

confidence: 99%

Thermodynamic Overview of Bioconjugation Reactions Pertinent to Lysine and Cysteine Peptide and Protein Residues

Lopandic,

Merza,

Honek

2023

Compounds

View full text Add to dashboard Cite

show abstract

Gold(I) NHC Catalysts Immobilized to Amphiphilic Block Copolymers: A Versatile Approach to Micellar Gold Catalysis in Water

et al. 2022

View full text Add to dashboard Cite

Fifteen gold(I)-NHC-functionalized amphiphilic block copolymers that differ in the type of linker (ethyl, pentyl, octyl and benzyl) that attaches the gold(I) NHC catalyst to the block copolymer backbone, as well as, the substitution pattern of the NHC ligand (i. e. mesityl, methyl, 2,6-diisopropylphenyl and nhexyl) were synthesized by a reversible addition and fragmentation transfer (RAFT) polymerization process. Micelle formation of the gold(I) NHC polymers was analyzed by electron microscopy and dynamic light scattering and revealed spherical and rod-like particles from 12 to 96 nm. In the micellar, gold(I) catalyzed cycloisomerization of an allene to the corresponding dihydrofuran, linker flexibility and substitution pattern of the NHC-ligand showed a strong effect on the catalytic activity. Best results were obtained were obtained for gold(I) NHC catalysts bound to the polymer backbone by pentyl linker whereas the rather stiff benzyl linker gave lowest catalyst conversion. Moreover, the polymer catalyst could be recycled in four consecutive runs and gave activities from 35 to 84 % in the fourth run and underscores the importance of fine tuning structural parameters to achieve high conversion under micellar reaction conditions.

show abstract

NKT-cell glycolipid agonist as adjuvant in synthetic vaccine

Liu

Guo

2017

Carbohydrate Research

View full text Add to dashboard Cite

Polyfluorophenyl Ester-Terminated Homobifunctional Cross-Linkers for Protein Conjugation

Cited by 7 publications

References 12 publications

Thermodynamic Overview of Bioconjugation Reactions Pertinent to Lysine and Cysteine Peptide and Protein Residues

Thermodynamic Overview of Bioconjugation Reactions Pertinent to Lysine and Cysteine Peptide and Protein Residues

Gold(I) NHC Catalysts Immobilized to Amphiphilic Block Copolymers: A Versatile Approach to Micellar Gold Catalysis in Water

NKT-cell glycolipid agonist as adjuvant in synthetic vaccine

Contact Info

Product

Resources

About