Incorporation of carbohydrates and peptides into large triazine-based screening libraries using automated parallel synthesis

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

“…Inverse electron demand Diels-Alder reaction of 1,2,4,5-tetrazines are well known in the literature. Cycloadditions with electron-rich alkynes [759,762,774,776,[781][782][783][784][785][786][787][788] or alkenes [602,762,772,773,781,784,[789][790][791][792] Zhou et al have described an alternative Diels-Alder route to the well-known C,C cycloaddition (Carboni-Lindsey reaction). Quantum mechanical calculations showed that N,N cycloaddition of alkenes and alkynes to s-tetrazines is possible.…”

( S )‐Leucine and [( S )‐1‐(1‐Naphthyl)ethyl]amine as Chiral Building Blocks for a Bifunctional System − Synthesis of a New Chiral Stationary Phase and Evaluation of Its Biselector Properties in the HPLC Resolution of Racemic Compounds

“…The disubstituted s-triazine derivative 2 was obtained according to a literature method used for preparing aminosubstituted s-triazine derivatives, [30] treating s-trichlorotriazine with an equimolar amount of N-BOC-ethanolamine in acetonitrile in the presence of DIPEA as a base. In view of the poor nucleophilicity of the hydroxy group, the reaction was carried out at 60°C in order to increase the degree of conversion of the substrate.…”

Glycopeptide and Oligosaccharide Libraries

“…Recently, a library of 640 carbohydrate triazine derivatives obtained by the reaction between p-aminophenyl pyranoside with cyanuric chloride was rapidly screened as inhibitors of the proteases Factor Xa and plasmin. [145] The synthesis of the libraries as parallel arrays of discrete compounds in 96-well plates facilitated the high-throughput screening of protease activity in the same plates using spectrophotometric measurement of the p-nitroaniline derivative released during substrate hydrolysis. No carbohydrate-based inhibitors were found.…”