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Photoresponsive nucleic acid manufacturing method

Foreign code F110004125
File No. RX02P34WO
Posted date Jul 11, 2011
Country EPO
Application number 09710413
Gazette No. 2253640
Gazette No. 2253640
Date of filing Feb 13, 2009
Gazette Date Nov 24, 2010
Gazette Date Jul 30, 2014
International application number JP2009000562
International publication number WO2009101810
Date of international filing Feb 13, 2009
Date of international publication Aug 20, 2009
Priority data
  • 2009JP000562 (Feb 13, 2009) WO
  • P2008-033713 (Feb 14, 2008) JP
Title Photoresponsive nucleic acid manufacturing method
Abstract The present invention provides a manufacturing method that can easily manufacture a compound known as photoresponsive (photocoupling) nucleic acids at high yield in a shorter period of time than that of the conventional technology.
The present invention relates to a method of manufacturing a photoresponsive nucleic acid which includes a step of reacting a nucleic acid having groups represented by the Formula I, the Formula III, the Formula IV, or the Formula V and a compound represented by the Formula II, or reacting a nucleic acid having groups represented by the Formula VI, the Formula VIII, the Formula IX, or the Formula X and a compound represented by the Formula VII by heating them by microwaves in the presence of a metal catalyst, a basic substance, and a solvent.
Scope of claims [claim1]
1. A method of manufacturing a nucleic acid having a group represented by the following Formula XI: (see diagramm)(in the Formula XI, X represents O, S or NH, R1 represents a hydrogen atom, a cyano group, a carboxamide group, an alkoxycarbonyl group, or a monovalent group of a substituted or unsubstituted aromatic compound, and R2 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a cyano group or a C1 to C6 acyl group.), wherein the method comprises the following step (a): (a) a nucleic acid having the Formula I as a base moiety: (see diagramm)(in the Formula I, X represents O, S or NH, and A1 represents a halogen atom.) is reacted with the compound that is represented by the following Formula II (see diagramm)(in the Formula II, R1 represents a hydrogen atom, a cyano group, a carboxamide group, an alkoxycarbonyl group, or a monovalent group of a substituted or unsubstituted aromatic compound, and R2 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a cyano group or a C1 to C6 acyl group.) in the presence of a palladium complex catalyst, a basic substance and a solvent by microwave heating; or a method of manufacturing a nucleic acid having a group represented by the following Formula XV: (see diagramm)(in the Formula XV, X represents O, S or NH, R4 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a cyano group or a C1 to C6 acyl group, and R3 represents a monovalent group of a substituted or unsubstituted aromatic compound, a hydrogen atom, a cyano group, a carboxamide group or an alkoxycarbonyl group.), wherein the method comprises the following step (b):(b) a nucleic acid having the Formula VI as a base moiety: (see diagramm)(in the Formula VI, X represents O, S or NH, R4 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a cyano group or a C1 to C6 acyl group, and A2 represents a halogen atom.) is reacted with the compound that is represented by the following Formula VII:

R 3-B(OH) 2 (VII)

(in the Formula VII, R3 represents a monovalent group of a substituted or unsubstituted aromatic compound, a hydrogen atom, a cyano group, a carboxamide group or an alkoxycarbonyl group.) in the presence of a palladium complex catalyst, a basic substance and a solvent by microwave heating.
[claim2]
2. The method according to Claim 1, comprising the step (a).
[claim3]
3. The method according to Claim 1, comprising the step (b).
[claim4]
4. The method according to Claim 1 or 2, wherein the step (a) is carried out by heating by microwaves in the presence of a palladium complex catalyst, a basic substance, a solvent, and an aqueous solution of carboxylate.
[claim5]
5. The method according to Claim 1 or 3, wherein the step (b) is carried out by heating by microwaves in the presence of a palladium complex catalyst, a basic substance, a solvent, and an aqueous solution of carboxylate.
[claim6]
6. The method according to any one of Claims 1 to 5, wherein the basic substance is trialkylamine having a C1 to C6 alkyl group.
[claim7]
7. The method according to Claim 1 or 2, wherein the step (a) is carried out by heating by microwaves in the presence of a palladium complex catalyst, a solvent, and an aqueous solution of carboxylate.
[claim8]
8. The method according to Claim 1 or 3, wherein the step (b) is carried out by heating by microwaves in the presence of a palladium complex catalyst, a solvent, and an aqueous solution of carboxylate.
[claim9]
9. The method according to any one of Claims 4 to 8, wherein the aqueous solution of carboxylate is an aqueous solution of an alkali metal salt of C1 to C3 carboxylic acid.
[claim10]
10. The method according to any one of Claims 4 to 9, wherein the aqueous solution of carboxylate is a buffer solution having a pH range of 4.5 to 6.0.
[claim11]
11. The method according to any one of Claims 1 to 10, wherein the heating by microwaves is carried out in the temperature range of 70 to 140 deg.C.
[claim12]
12. The method according to any one of Claims 1 to 11, wherein the heating by microwaves is carried out in the time range of 1 to 30 minutes.
[claim13]
13. The method according to any one of Claims 1 to 12, wherein the solvent is an aprotic polar solvent.
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • FUJIMOTO KENZO
  • OGINO MASAYUKI
  • YOSHIMURA YOSHINAGA
IPC(International Patent Classification)
Specified countries Contracting States: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR
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