Development of a new linker for the solid-phase synthesis of N-hydroxylated and N-methylated secondary amines

Pauli, Denise; Bienz, Stefan

doi:10.1016/j.tet.2013.12.014

Cited by 5 publications

(2 citation statements)

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“…The ninhydrine test is the most common approach used for primary amines, but it cannot be applied for secondary amines. Thus, for NMAA coupling, chloranil and NF‐31 tests are more suitable for monitoring purposes …”

Section: Growing the Peptide Chain Using Nmaa In Solid‐phasementioning

confidence: 99%

N‐methylation in amino acids and peptides: Scope and limitations

et al. 2018

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Active pharmaceutical ingredients (APIs) can be divided into two types, namely chemical and biological entities. Traditionally, the former has been associated with the so-called small molecules. The revival of peptides in pharmaceutical industry results from their importance in many biological roles. However, low metabolic stability and the lack of oral availability of most peptides is the main drawback for peptide to fulfill that paradigmatic situation. In this regard, efforts are being channeled into addressing this issue by introducing restrictions into the flexible peptide backbone, mainly through N-methyl amino acids (NMAAs) or development of small cyclic peptides. In many cases, both the above restrictions are combined with the aim to enhance oral availability. The synthesis of NMAAs is complex and their introduction into the peptide chain brings additional synthetic challenges and also sometimes leads to side-reactions. Here we discuss the most efficient methods for the synthesis of NMAAs (either in solution or in solid phase) and also their introduction into peptide sequences. Special attention is also given to the detection of side reactions and the most efficient way to prevent them.

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Section: Growing the Peptide Chain Using Nmaa In Solid‐phasementioning

confidence: 99%

N‐methylation in amino acids and peptides: Scope and limitations

et al. 2018

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“…[35][36][37][38] Historically, (co)polymers of vinyl benzyl chloride have been used in Merrifield resins that are part of solid phase synthesis, in gas chromatography, phase transfer catalysis and many other applications. [39][40][41][42][43][44][45][46] To the best of our knowledge, there is no report detailing the facile preparation of poly(vinyl quaternary ammonium chloride)s with varying quaternary ammonium species starting from 4-vinyl benzyl chloride, except for two reports that contain specific derivatives such as poly(vinyl benzyl trimethylammonium chloride) and 4-vinyl benzyl dimethylhexadecylammonium chloride. [47][48][49] Considering that benzalkyl ammonium chlorides are widely used 50 as disinfectants, ophthalmic preservatives and antiseptics, quaternary ammonium polymers obtained by the quaternization of homo-and copoly(4-vinyl benzyl chloride) can be potentially used as antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%