Recycling the versatile Pipecolic linker.
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.
Zajdel
Pawel
P
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.
Masurier
Nicolas
N
Sanchez
Pierre
P
Pawlowski
Maciej
M
Kreiter
Aude
A
Nomezine
Gaël
G
Enjalbal
Christine
C
Amblard
Muriel
M
Martinez
Jean
J
Subra
Gilles
G
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry
D010875:Pipecolic Acids; D014269:Trifluoroacetic Acid