The spin-labelled, cyclic, chiral beta-amino acids cis-beta-TOAC and trans-beta-TOAC, have been synthesised in an enantiomerically pure form by amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)- or (S)-alfa-methyl-benzylamine, followed by reduction with NaBH3CN/CH3COOH or NaBH4/(CH3)2CHCOOH. The 3D-structure of the hexapeptide 1, prepared by 4+2 segment coupling in solution, has been preliminarily analyzed by spectroscopic techniques.
Synthesis of the spin-labelled beta-amino acids cis- and trans-beta-TOAC, and conformational study of a trans-beta-TOAC/ACHC hexapeptide
FORMAGGIO, FERNANDO;PEGGION, CRISTINA;TOFFOLETTI, ANTONIO;CORVAJA, CARLO;TONIOLO, CLAUDIO
2005
Abstract
The spin-labelled, cyclic, chiral beta-amino acids cis-beta-TOAC and trans-beta-TOAC, have been synthesised in an enantiomerically pure form by amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)- or (S)-alfa-methyl-benzylamine, followed by reduction with NaBH3CN/CH3COOH or NaBH4/(CH3)2CHCOOH. The 3D-structure of the hexapeptide 1, prepared by 4+2 segment coupling in solution, has been preliminarily analyzed by spectroscopic techniques.
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