A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles

Abstract

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Supramolecular Ligands for Histone Tails by Employing a Multivalent Display of Trisulfonated Calix[4]arenes

“…Thus, we designed CA1 ( 1 ), CA2 ( 2 ), and CA3 ( 3 ) with one, two, or three trisulfonated calix[4]arenes, respectively (Scheme B; syntheses in Scheme ). Starting from protected lysine 4 , introduction of a linker followed by masking its end as an acetamide and removal of the Boc group afforded primary amine 6 . Conjugation with trisulfonated calix[4]arene carboxylic acid ( 12 ) in the presence of dicyclohexylcarbodiimide (DCC) and oxyma provided monovalent 1 in good yield.…”

“…[13] Thus, we designed CA1 (1), CA2 (2), and CA3 (3)w ith one, two,o rt hree trisulfonated calix [4]arenes, [14] respectively (Scheme 1B;s yntheses in Scheme2). Starting from protected lysine 4, [15] introduction of al inker followed by maskingi ts end as an acetamide and removalo ft he Boc group afforded primary amine 6.C onjugation with trisulfonated calix [4]arene carboxylic acid( 12) [14] in the presence of dicyclohexylcarbodiimide (DCC) and oxyma provided monovalent 1 in good yield. Simi-larly,t he introduction of linkers by using acetyl-and/or Fmocprotected building blocks 10 and 11 to 4,f ollowed by global deprotection,a fforded di-and tri-valentp rimary amines, respectively.F inally,c onjugation of 12 under the same conditions provided divalent 2 andt rivalent 3 in good yields.…”

Solvent-Free Synthesis of α-Amino Nitrile-Derived Ureas

“…In the context of a medicinal chemistry project focused on the search for modulators of protein–protein interactions, we required the basic amino acid derived N -(cyanomethyl)ureas of general formula A (Scheme ), which were expected to be easily accessible from the corresponding α-amino nitriles B , by reaction with isocyanates. These α-amino nitriles B were previously obtained by a modified Strecker synthesis as epimeric mixtures in the carbon bearing the cyano group, which were chromatographically resolved …”