O-Succinimidyl-1,3-dimethyl-1,3-trimethyleneuronium salts as efficient reagents in active ester synthesis

Bailen, Miguel A.; Chinchílla, Rafael; Dodsworth, David J.; Nájera, Carmén

doi:10.1016/s0040-4039(02)00090-4

Cited by 14 publications

(3 citation statements)

References 27 publications

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“…However, this reactant has to be prepared from toxic 1,1,3,3-tetramethylurea (TMU). In 2002, Bailén et al 44 reported the use of O-succinimidyl-1,3-dimethyl-1,3trimethyleneuronium salts as efficient reagents in NHS-ester synthesis. The corresponding hexafluorophosphate salt (HSDU) or tetrafluoroborate salt (TSDU) have been prepared from less toxic and inexpensive 1,3-dimethylpropylurea (DMPU).…”

Section: Scheme 5 Kim's Approach For the Synthesis Of Nhs-estersmentioning

confidence: 99%

An Overview of the Synthesis of Highly Versatile N-Hydroxysuccinimide Esters

et al. 2016

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N-Hydroxysuccinimide esters (NHS-esters) are important and widely used tools in various areas of chemistry including peptide synthesis, bioconjugate chemistry, functionalized materials and polymers. The usual strategy employed to prepare these active esters generally relies on the coupling reaction with a carboxylic acid and N-hydroxysuccinimide in the presence of a coupling agent. However, more recently, many other efficient strategies have emerged in the literature. This short review covers the literature devoted to the preparation of these valuable N-hydroxysuccinimide esters. 1 Introduction 2 N-Hydroxysuccinimide Coupling Reaction with Activated Carboxylic Acids 3 Carboxylic Acid Coupling Reaction with Activated N-Hydroxysuccinimide 4 Alcohol and Aldehyde Coupling Reaction with N-Hydroxysuccinimide under Oxidizing Conditions 5 Carbonylative Cross-Coupling Reaction 6 Conclusion

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Section: Scheme 5 Kim's Approach For the Synthesis Of Nhs-estersmentioning

confidence: 99%

An Overview of the Synthesis of Highly Versatile N-Hydroxysuccinimide Esters

et al. 2016

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“…However, the use of EDAC is undesirable in large scale pharmaceutical applications as it creates toxic aqueous waste streams . Succinimidyl ester formation without carbodiimides can be accomplished with activated derivatives of N -hydroxy-succinimide, and the use of the carbonate, oxalate, phosphonate, and uronium salts of N -hydroxysuccinimide have been reported. , However, these NHS derivatives are not commercially available and need to be synthesized and isolated prior to use, adding an additional step to the overall formation of the desired succinimidyl ester …”

mentioning

confidence: 99%

In Situ Formation of N-Trifluoroacetoxy Succinimide (TFA-NHS): One-Pot Formation of Succinimidyl Esters, N-Trifluoroacetyl Amino Acid Succinimidyl Esters, and N-Maleoyl Amino Acid Succinimidyl Esters

Leonard

Brunckova

2011

J. Org. Chem.

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A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.

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“…[1] For example, several methods have been developed using dicyclohexylcarbodiimide, [2] Ph 3 P=diethyl azodicarboxylate, [3] bis(N-succinimidyl) carbonate, [4] 2-pyridyl carbonate, [5] N,N,N 0 ,N 0 -tetramethyl(succinimido)uronium tetrafluoroborate, [6] chloro phosphate, [7] 3-(dimethylamino)propylcarbodiimide, [8] O-succinimidyl-1,3-dimethyl-1,3-trimethyleneuronium salts, [9] and 1-ethyl-3-(3 0 -dimethylaminopropyl) carbodiimide. [10] However, these are not free from some drawbacks such as by-product formation, limited availability, inconvenient handling, or poor stability.…”

mentioning

confidence: 99%