SPANISH NATIONAL RESEARCH COUNCIL (CSIC)
Modified carbohydrates as a building blocks for the synthesis of nucleosides
CSIC and Natural Products and Glycotechnology (NPG) Research institute have developed a method
for the synthesis of nucleosides starting from modified carbohydrates. The process is very selective, and
a wide range of nucleosides with different functional groups can be obtained. The method could be
useful for the synthesis of nucleosides with applications as drugs or as intermediates for the synthesis of
oligonucleotides. We are looking for a company for a licence agreement.
An offer for patent licence
Description of the offer
The development of methods for the synthesis of nucleosides has a great
importance due to the increase, in the last years, of drugs and therapeutic
procedures based on the use of oligonucleotides and modified nucleosides. Being
highly functionalized compounds, nucleoside synthesis is not easy, and new and
more efficient methods for their selective preparation are needed.
Most of the methods are based on the glycosylation of a nucleobase with a
carbohydrate, but one of the problems of this reaction is their poor selectivity,
decreasing the yield of the final product. On the other hand, previous methods
need to operate with strong acids at elevated temperatures, and only work with
very specific substrates, limiting the scope of products that can be obtained.
It has been developed a new method for the formation of glycosilic bond, starting
from modified sugars. Intermediates are easily prepared and the reaction is higly
stereoselective, obtaining the desired isomer. Furthermore, the reactions are
performed under mild conditions and the precursors admit a wide range of
functional and protecting groups, which makes them especially useful for the
synthesis of oligonucleotides and modified nucleosides.
The products could we used as building
blocks for the synthesis of modified
oligonucleotides
Schematic picture how antisense DNA
oligonucleotide prevents protein
translation (Robinson R, 2004,
reproduced under CCA 2.5 Generic
license)
Innovative aspects and advantages
 Carbohydrate precursors are easily obtained from commercially available
products
 Compared to previous methods for the synthesis of nucleosides, where
mixtures of isomers are obtained, the new method allows the formation of
glycosilic bond stereoselectively (only one isomer is detected) with very good
yield
 Previous glycosylation methods require hard conditions (strong acids at
elevated temperatures) and only very specific substrates and protecting groups
are allowed; with the new method is possible to operate at room temperature
using catalytic amounts of acid, and a wide range of protecting group can be
used
 Glycosylation reaction can be performed in the presence of phosphate groups,
therefore the products could be used in the synthesis of oligonucleotides
Patent Status
Spanish patent application filed
For further information,
please contact
Luis Miguel Lozano, Ph.D.
Institute of General Organic
Chemistry/ Deputy Vice-Presidency
for Knowledge Transfer
Spanish National Research Council
(CSIC)
Tel.: + 34 – 91 562 29 00
Fax: + 34 – 91 564 48 53
E-mail: [email protected]