D-luciferin, D-luciferin derivative, precursor of these compounds and method for producing these compounds
AssigneesKanto Denka Kogyo Co., Ltd., Kinki University
InventorsKouichi Matsumoto, Masafumi Kobayashi
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Abstract
To establish an unprecedented novel method for producing D-luciferin and a D-luciferin derivative without using expensive 2-cyano-6-hydroxybenzothiazole that is obtained by a multi-stage production process. In the method for producing D-luciferin and a D-luciferin derivative, the above object is achieved via a novel substituted diaminodithioether represented by the following formula (1): wherein X is H, OCH3 or OH; and Y, Z and W are H or monovalent organic groups, which serves as a precursor.
Claims15
A substituted diaminodithioether represented by the following formula (1):
- wherein X is H, OCH3 or OH;
- and Y, Z and W are H or monovalent organic groups selected from the group consisting of alkyl groups, N, N-disubstituted amino groups, alkoxy groups, aryl groups, and aryloxy groups.
A method for producing a substituted diaminodithioether represented by the following formula (1):
- wherein X is H, OCH3 or OH;
- and Y, Z and W are H or monovalent organic groups selected from the group consisting of alkyl groups, N, N-disubstituted amino groups, alkoxy groups, aryl groups, and aryloxy groups, the method comprising the step of:
- (a) reacting a substituted D-cysteine represented by the following formula (2):
- with an o-aminobenzenethiol derivative represented by the following formula (3):
- wherein X is H, OCH3 or OH;
- and Y, Z and W are H or monovalent organic groups selected from the group consisting of alkyl groups, N, N-disubstituted amino groups, alkoxy groups, aryl groups, and aryloxy groups, in the presence of a base.
A method for producing D-luciferin and a D-luciferin derivative represented by the following formula (4):
- wherein X is H, OCH3 or OH;
- and Y, Z and W are H or monovalent organic groups selected from the group consisting of alkyl groups, N, N-disubstituted amino groups, alkoxy groups, aryl groups, and aryloxy groups, the method comprising the step of:
- (b) cyclizing substituted diaminodithioether represented by formula (1)
- in the presence of a base.
A method for producing a substituted diaminodithioether represented by the following formula (1):
- wherein X is H, OCH3 or OH;
- and Y, Z and W are H or monovalent organic groups selected from the group consisting of alkyl groups, N, N-disubstituted amino groups, alkoxy groups, aryl groups, and aryloxy groups, the method comprising the step of:
- (c) reacting an aminothioether derivative represented by the following formula (5):
- wherein X, Y, Z and W are as described above, with D-cysteine in the presence of a base.
Dependencies are inferred from the claim text.