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US 10,472,383 B2Granted
Nucleoside triphosphates with stable aminoxy groups
OwnerSteven A Bennerinventor
Life of this patent
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Abstract
This invention claims aqueous compositions that comprise triphosphates of 2′-deoxynucleoside derivatives that have, instead of a 3′-OH moiety, a 3′-ONH2 moiety; wherein said compositions contain less than 0.5 mole percent contaminating triphosphate having a 3′-OH moiety, as well as processes for providing such compositions. The compositions further must contain insubstantial amounts of hydroxylamine.
Claims15
A composition comprising an aqueous solution containing an alkoxylamine, hydroxylamine at a concentration of less than 1 micromolar and a molecule having the structure:
- or one of its ionized forms, wherein B is a heterocycle selected from the group consisting of
- wherein Su indicates the point of attachment of the heterocycle to the sugar, R is either H, CH3, or a functionalized side chain, and X is either N or C—R.
A process for preparing a compound of having the structure:
- or one of its ionized forms, wherein B is a heterocycle selected from the group consisting of
- wherein Su indicates the point of attachment of the heterocycle to the sugar, R is H, CH3, or a functionalized side chain, and X is either N or C—R, wherein said process comprises:
- (a) contacting a solid phase having an immobilized aldehyde or ketone moiety with compound having the following structure
- wherein Q is either H or a dimethoxytrityl group, and B is a heterocycle selected from the group consisting of
- wherein Su indicates the point of attachment of the heterocycle to the sugar, R is H, CH3, or a functionalized side chain, and X is either N or C—R, followed by
- (b) contacting the composition from step (a) with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one, followed by
- (c) contacting the composition from step (b) with an ammonium salt of a pyrophosphate, followed by
- (d) oxidizing the composition from step (c), followed by
- (e) washing the composition from step (d) with an aqueous solution comprising an alkoxylamine.
6 more elements
Dependencies are inferred from the claim text.