title: A versatile annulation protocol toward novel constrained phosphinic peptidomimetics.
abstract: The development of a novel 3-center 2-component annulation reaction between alpha,omega-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting alpha,omega-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochemistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structures.
authors: Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou 15771, Athens, Greece.
authors: Magdalini
authors: M
authors: Nasopoulou
authors: Dimitris
authors: D
authors: Georgiadis
authors: Magdalini
authors: M
authors: Matziari
authors: Vincent
authors: V
authors: Dive
authors: Athanasios
authors: A
authors: Yiotakis
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D003500:Cyclization; D005449:Fluorenes / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D010721:Phosphinic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D010875:Pipecolic Acids / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D010721:Phosphinic Acids; D010875:Pipecolic Acids