Phenyl esters, preferred reagents for mono-acylation of polyamines in the presence of water

Pappas, Kyrie; Zhang, Xiang; Tang, Wenxian; Fang, Shiyue

doi:10.1016/j.tetlet.2009.07.142

Cited by 14 publications

(6 citation statements)

References 15 publications

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“…The aglycones were synthesized by a common pathway (Scheme ). Commercially available diamino alkanes were converted to monobenzoylated species 1a , b by treatment with methyl benzoate. , The resulting primary amine underwent a Michael addition with acrylamide 2 , and the resulting secondary amine was acylated with the appropriate acyl chloride to give aglycones 3a – c in a one-pot series of reactions. Purification steps were either recrystallization or silica chromatography without the need for high-separation resolution.…”

Section: Resultsmentioning

confidence: 99%

Improved Reagents for Newborn Screening of Mucopolysaccharidosis Types I, II, and VI by Tandem Mass Spectrometry

et al. 2014

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Tandem mass spectrometry for the multiplex and quantitative analysis of enzyme activities in dried blood spots on newborn screening cards has emerged as a powerful technique for early assessment of lysosomal storage diseases. Here we report the design and process-scale synthesis of substrates for the enzymes α-l-iduronidase, iduronate-2-sulfatase, and N-acetylgalactosamine-4-sulfatase that are used for newborn screening of mucopolysaccharidosis types I, II, and VI. The products contain a bisamide unit that is hypothesized to readily protonate in the gas phase, which improves detection sensitivity by tandem mass spectrometry. The products contain a benzoyl group, which provides a useful site for inexpensive deuteration, thus facilitating the preparation of internal standards for the accurate quantification of enzymatic products. Finally, the reagents are designed with ease of synthesis in mind, thus permitting scale-up preparation to support worldwide newborn screening of lysosomal storage diseases. The new reagents provide the most sensitive assay for the three lysosomal enzymes reported to date as shown by their performance in reactions using dried blood spots as the enzyme source. Also, the ratio of assay signal to that measured in the absence of blood (background) is superior to all previously reported mucopolysaccharidosis types I, II, and VI assays.

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Section: Resultsmentioning

confidence: 99%

Improved Reagents for Newborn Screening of Mucopolysaccharidosis Types I, II, and VI by Tandem Mass Spectrometry

et al. 2014

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“…To evaluate our system properties on a model reaction, the acetylation of anilines (Scheme ) was chosen. Indeed, the acetylation of amines and anilines is an important and widely used transformation in organic synthesis, and a number of reagents coupled with promoters or catalysts have been put forth. − With the aim of performing microreactions in aqueous media, acid halides and acid anhydrides are usually employed . Few other strategies have been reported in the literature, especially with acetic anhydride in sodium dodecyl sulfate (SDS) media .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of a Photochromic Surfactant for Organic Reactions in Aqueous Media

et al. 2012

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A novel photochromic azobenzene-based surfactant was described for organic chemistry in water. The molecule 4-butylazobenzyl-4'-triazologlucuronic acid sodium salt thus synthesized can be isomerized from its trans to its cis form reversibly in solution by simple light irradiation. That property allowed the recyclability of a model acetylation reaction performed in the surfactant media, compared to the well-known, commercially available sodium dodecyl sulfate surfactant media.

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“…Under these conditions, mono-acylation of the symmetric diamine was favored over di-acylation, which is a common side reaction observed in mono-acylation of diamines. [23][24][25] Compound 4 was acylated with methacrolyl chloride using DIEA as a base to give 5. Converting 5 to 6a-d was achieved by first treating 5 with excess acetyl chloride.…”

Section: Synthesis Of Methacrylation Phosphoramidites 1a-dmentioning

confidence: 99%

Polymerizable phosphoramidites with an acid-cleavable linker for eco-friendly synthetic oligodeoxynucleotide purification

Pokharel

Fang

2016

Green Chem.

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Methacrylation phosphoramidites containing a linker cleavable with acetic acid were synthesized, and used for synthetic oligodeoxynucleotide (ODN) purification. During automated synthesis, the full-length ODN was tagged with the phosphoramidite. The failure sequences were not. In purification, the fulllength ODN was co-polymerized into a polyacrylamide gel, and the failure sequences and other impurities were removed by washing. Pure ODN was cleaved from the gel with 80% acetic acid. Using this method, purification of sequences as long as a 197-mer, which are from the phi29 DNA polymerase gene, and at scales as large as 50 μmol was demonstrated. The products have high purity and the recovery yields are high. The method does not use any type of chromatography and purification is achieved through simple manipulations such as shaking and filtration. Compared with gel electrophoresis and HPLC purification methods, the new technology is less labor-demanding and more amendable for automation, consumes a smaller amount of environmentally harmful organic solvents and requires little energy for solvent evaporation. Therefore, it is ideal for high throughput purification and large scale ODN-based drug purification as well as small scale purification. † Electronic supplementary information (ESI) available. See

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Phenyl esters, preferred reagents for mono-acylation of polyamines in the presence of water

Cited by 14 publications

References 15 publications

Improved Reagents for Newborn Screening of Mucopolysaccharidosis Types I, II, and VI by Tandem Mass Spectrometry

Improved Reagents for Newborn Screening of Mucopolysaccharidosis Types I, II, and VI by Tandem Mass Spectrometry

Synthesis and Evaluation of a Photochromic Surfactant for Organic Reactions in Aqueous Media

Polymerizable phosphoramidites with an acid-cleavable linker for eco-friendly synthetic oligodeoxynucleotide purification

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