Chiral peptide nucleic acids
AssigneeIsis Innovation Limited
InventorGordon Lowe
Life of this patent
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Abstract
Chiral peptide nucleic acids are provided which hybridise strongly with complementary nucleic acids and have potential as antigene and antisense agents and as tools in molecular biology. Compounds with cis-stereochemistry and based on proline and a spacer amino acid have structures (II), (III), where n is 1 or 2-200, B is a protected or unprotected base, R is H or alkyl, aralkyl or heteroaryl and may be substituted, X may be OH, and Y may be H.
Claims5
A compound of formula (IV)
- where R2 is H or a protecting group,
- R3 is H or a protecting group compatible with R2, and
- B is a protected or unprotected heterocyclic base capable of Watson-Crick or Hoogsteen pairing.
A compound of formula (V)
- where R2 is diphenylmethyl, and
- R3 is t-butoxycarbonyl.
A method of making a compound of formula (V) which method comprises converting a diphenylmethyl ester of N-t-butyoxycabonyl-cis-r-hydroxy-D-proline by a Mitsunobu reaction in the presence of formic acid to give an inverted formate ester which is aminolysed to provide the diphenylmethyl ester of N-t-butoxycarbonyl-trans-4-hydroxy-D-proline (V).
Dependencies are inferred from the claim text.