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, Nicholas M.; Brunckova, Jarmila

doi:10.1021/jo201686e

Cited by 19 publications

(25 citation statements)

References 41 publications

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“…Hydrolysis of the dimethyl ester 12 used LiOH as before. The bis-NHS ester 14 was prepared using in situ generated TFA-NHS, 17 which lead to similar overall yields but shorter reaction times, fewer side products, and a more reliable purification. Finally, oxidation to the bissulfoxide as previously described gave azide 3 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein–protein interactions by mass spectrometry

et al. 2015

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The cross-linking Mass Spectrometry (XL-MS) technique extracts structural information from protein complexes without requiring highly purified samples, crystallinity, or large amounts of material. However, there are challenges to applying the technique to protein complexes in vitro, and those challenges become more daunting with in vivo experiments. Issues include effective detection and identification of cross-linked peptides from complex mixtures. While MS-cleavable cross-linkers facilitate the sequencing and identification of cross-linked peptides, enrichable cross-linkers increase their detectability by allowing their separation from non-cross-linked peptides prior to MS analysis. Although a number of cross-linkers with single functionality have been developed in recent years, an ideal reagent would incorporate both capabilities for XL-MS studies. Therefore, two new cross-linkers have been designed and prepared that incorporate an azide (azide-A-DSBSO) or alkyne (alkyne-A-DSBSO) to enable affinity purification strategies based on click chemistry. The integration of an acid cleavage site next to the enrichment handle allows easy recovery of cross-linked products during affinity purification. In addition, these sulfoxide containing cross-linking reagents possess robust MS-cleavable bonds to facilitate fast and easy identification of cross-linked peptides using MS analysis. Optimized, gram-scale syntheses of these cross-linkers have been developed and the azide-A-DSBSO cross-linker has been evaluated with peptides and proteins to demonstrate its utility in XL-MS analysis.

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Section: Resultsmentioning

confidence: 99%

“…The dimethyl ester was hydrolyzed to a diacid using LiOH, and the di-NHS ester was prepared using TFA-NHS reagent. 17 Di-NHS ester 20 was isolated in 60% yield using this method. The same compound was also prepared using an EDCI coupling, but the yield was lower and the purification was more difficult.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein–protein interactions by mass spectrometry

et al. 2015

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“…SMCC is an FDA-approved linker commonly used in bioconjugation and was synthesised in accordance with the literature procedure. [34][35][36] It was coupled to SMCC by means of the NHS ester in a loading of 76 % (Scheme 4). This reaction is quick, specific and leaves the maleimide free to couple to the thiol.…”

Section: Scheme 1 Synthesis Of Sugarmentioning

confidence: 99%

Immobilization of UDP‐Galactose on an Amphiphilic Resin

et al. 2018

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Nucleotide sugars are activated sugar precursors used by glycosyltransferases to form glycans. Here we report the first examples of resin‐bound nucleotide sugars: fluorinated UDP‐galactose and UDP‐galactose. They were conjugated to a polyethylene glycol resin through the C6 position with an SMCC linker in good to excellent yields. This synthesis represents an efficient method to access resin‐bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation. The system has been conceived as a new chemistry‐based screening system for enzymes that use UDP‐galactose.

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“…NMR spectra were measured on Bruker AV-400 High Performance Digital NMR Spectrometer ( 1 H at 400 MHz, 13 C at 100 MHz). The 1 H NMR spectra were calibrated against the peak of tetramethylsilane (TMS, 0 ppm) and the 13 C NMR spectra were calibrated against the peak of CDCl 3 (77.0 ppm). Data for 1 H NMR spectra were reported as follows: chemical shift (ppm), peak shape (s ¼ singlet,…”

Section: Nmr and Mass Analysismentioning

confidence: 99%

A linker approach to phospholipopeptides

Liang

2015

Euro J Lipid Sci & Tech

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Peptides and phospholipids are important macromolecules in both the chemistry and biology fields, but phospholipopeptides are barely found in nature and have not been studied. Here, we report a novel and efficient approach to the synthesis of phospholipidpeptides. By utilizing cross-linkers, phospholipopeptides from peptides with varied sequences and lengths were produced from phosphatidylethanolamine at high (>90%) yield, mild conditions and good applied scopes for multiple substrates. Synthetic phospholipopeptides containing bioactive peptide sequences may serve as therapeutics for a wide range of biomedical applications.Practical applications: Phospholipopeptides are prone to hydrolysis by the endogenous phospholipase activity in cells. Synthetic phospholipopeptides containing a bioactive peptide sequences may serve as therapeutics for a wide range of biomedical applications.

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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

Cited by 19 publications

References 41 publications

Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein–protein interactions by mass spectrometry

Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein–protein interactions by mass spectrometry

Immobilization of UDP‐Galactose on an Amphiphilic Resin

A linker approach to phospholipopeptides

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