Poly(beta-malic acid), PMLA, was first synthesized with the aim of bei
ng used as a macromolecular prodrug. However, this biodegradable polym
er is now the parent compound of a large family of functional polymers
, copolymers and polystereoisomers. The requirement for high molecular
weight polymers for a series of temporary therapeutic or specific app
lications needs to be conducted to examine the different steps of the
synthesis route starting from either racemic or chiral aspartic acid.
Drastic purifications of the intermediate products and of the beta-sub
stituted-beta-lactone used as monomer has allowed the synthesis of pol
ymers with high molecular weights, in a reproducible manner. In the ca
se of racemic poly(beta-malic acid benzyl ester), a precursor of PMLA,
it is now possible to prepare polymers with a M(SEC) superior to 150
000 (polystyrene standards). The specific catalytic hydrogenolysis of
the lateral benzyl protecting groups can be carried out and leads to t
he corresponding PMLA with long molecular chains, which are necessary
for certain applications in vivo. The results have been extended to di
fferent racemic and optically active derivatives of this poly(3-hydrox
y acid) ester type. Consequently, reproducible characteristics of the
corresponding polymeric materials can be obtained. Copyright (C) 1996
Elsevier Science Ltd.