BIODEGRADABLE POLYMERIC

MATERIALS FROM METABOLIC

SYNTHONS

Cornell university people projects

SYNTHON

 A synthon is a concept in retro synthetic

analysis

 Defined as a structural unit within a molecule

which is related to a possible synthetic
operation
NATURE OF HUMAN BODY

 The human body is a rich source of potential

building blocks that can be used to
synthesize new biomaterials, which upon
degradation are removed from the body via
their natural metabolic pathway(s)
ADVANTAGES
 Biomaterials synthesized from metabolic
synthons have advantages such as improved
biocompatibility and minimal build-up of
toxic degradation products in the body.
 In addition, a number of commodity and
specialty polymers are derived from
petrochemical building blocks, and do not
degrade to appreciable extents in the
environment.
 Interest in biodegradable polymers from
renewable resources has amplified as
petrochemical sources and available landfill
space begin to dwindle.
DIHYDROXYACETONE (DHA)
FOCUS OF PROJECT
 Focus is on the synthesis of new biodegradable
polymers based on the three carbon ketose,
dihydroxyacetone.
 DHA is a metabolite of glucose in humans and is
manufactured as a fermentative product of both
corn syrup and methanol. DHA is also approved
by the governmental regulatory agencies for
human consumption
 However, polymerization of DHA into
characterizable materials has been challenging
because it is in equilibrium with its dimer in
solution, and is susceptible to nucleophilic attack
at the C2 carbon. To date there are no published
reports of well-defined polymers derived from
DHA.
 Research group has discovered how to
synthesize three different classes of
polymeric materials derived from DHA:
polycarbonates, poly(carbonate-acetal)s and
polyspiroacetals.

 Each synthetic route was designed to have a

minimum number of steps to enhance their
potential economic viability

 The properties of these materials are

intriguing and have a number of potential
applications. For example, their initial results
show that the deprotected form of DHA
polycarbonate (V, Scheme 1A) strongly
adheres to proteins. These materials are
being investigated for their potential as
application as bioadhesives
The poly(carbonate-acetal)s in Scheme 1B are
thermally resistant (Td > 300°C), but the
acetal linkage provides a handle to tailor their
rate of degradation in the environment
 These materials are currently being
investigated for their ability to control the
rate of pesticide release into crop fields
 Lastly, the polyspiroacetals of 1C are
insoluble in aqueous solvents, but their
surfaces are hydrophilic with H2O contact
angles equal to polyethylene oxide (Θ ~57
°).
Thank you