Synthesis, characterisation and conformational studies of lipophilic, amphiphilic and water-soluble C-glyco-conjugated porphyrins

Synthesis, stereodisposition and nonplanar macrocyclic distortions of the four compounds 1-4 obtained from pyrrole, BF3. OEt2 and isopropylidene-protected D-glyceraldehyde, were investigated. Experiments of selective deprotection of these lipophilic compounds, depending both on the starting porphyrins stereodisposition and on the deprotecting agent (TFA) concentration, were carried out on such macrocycles, bearing easily removable protecting groups, to obtain water-soluble (5 and 8) and amphiphilic (6 and 7) porphyrins. Reactions of these macrocycles with Zn(II)-, Pd(II)-, Rh(II)-, Pb(II)-, Cu(II)- and Ni(II)-acetate, and the subsequent deprotection of compounds 9 and 13 affording the corresponding water-soluble C-glyco-porphyrinates (17 and 18) were studied. In the absence of crystals for X-ray studies, computational simulations were carried out to analyse the structural behaviour of some of these compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.