title: Recycling the versatile Pipecolic linker.
abstract: The Pipecolic linker is a new highly versatile handle which immobilizes on solid support through a carboxylic acid function a wide range of amines, alcohols, and hydrazines. The anchoring step on pipecolic resin is very easy and efficient, and compounds are released with high purities upon acidic treatment. During this treatment, an oxazolonium intermediate is hydrolyzed, yielding the cleavage of ester or amide bond and the release of free carboxylic acid of the starting linker. In this study, we report the possibility of recycling the pipecolic resin after the use of several trifluoroacetic acid (TFA) cleavage cocktails. We demonstrate that it can be reused up to five times without significant loading decrease.
authors: IBMM, Institut des Biomolécules Max Mousseron, UMR 5247, Universités Montpellier I and II, CNRS, Faculté de Pharmacie, 15 av. C. Flahault, BP 14491, 34093 Montpellier Cedex 05, France.
authors: Pawel
authors: P
authors: Zajdel
authors: Nicolas
authors: N
authors: Masurier
authors: Pierre
authors: P
authors: Sanchez
authors: Maciej
authors: M
authors: Pawlowski
authors: Aude
authors: A
authors: Kreiter
authors: Gaël
authors: G
authors: Nomezine
authors: Christine
authors: C
authors: Enjalbal
authors: Muriel
authors: M
authors: Amblard
authors: Jean
authors: J
authors: Martinez
authors: Gilles
authors: G
authors: Subra
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D010875:Pipecolic Acids; D014269:Trifluoroacetic Acid