Modified nucleotides
DC CAFCFirst Claim
1. A modified nucleotide molecule comprising a purine or pyrimidine base and a ribose or deoxyribose sugar moiety having a removable 3′
- -OH blocking group covalently attached thereto, such that the 3′
carbon atom has attached a group of the structure
—
O-Zwherein Z is any of —
C(RIV)2—
O—
R″
, —
C(R′
)2—
N(R″
)2, —
C(R′
)2—
N(H)R″
, —
C(RIV)2—
S—
R″ and
—
C(R′
)2—
N3,wherein —
C(RIV)2—
O—
R″
is of the formula —
CR4(R5)—
O—
CR4(R5)—
OR6 or of the formula —
CR4(R5)—
O—
CR4(R5)—
SR6; and
wherein —
C(RIV)2—
S—
R″
is of the formula —
CR4(R5)—
S—
CR4(R5)—
OR6 or of the formula —
CR4(R5)—
S—
CR4(R5)—
SR6;
wherein each R″
is or is part of a removable protecting group;
each R′
is independently a hydrogen atom, an alkyl, substituted alkyl, arylalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclic, acyl, cyano, alkoxy, aryloxy, heteroaryloxy or amido group, or a detectable label attached through a linking group;
or (R′
)2 represents an alkylidene group of formula ═
C(R′
″
)2 wherein each R′
″
may be the same or different and is selected from the group comprising hydrogen and halogen atoms and alkyl groups;
each R4 and R5 is independently a hydrogen atom or an alkyl group;
R6 is alkyl, cycloalkyl, alkenyl, cycloalkenyl or benzyl; and
wherein said molecule may be reacted to yield an intermediate in which each R″
is exchanged for H, which intermediate dissociates under aqueous conditions to afford a molecule with a free 3′
OH;
with the proviso that where Z is —
C(RIV)2—
S—
R″
, both RIV groups are not H.
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Accused Products
Abstract
The invention provides modified nucleotide or nucleoside molecule comprising a purine or pyrimidine base and a ribose or deoxyribose sugar moiety having a removable 3′-OH blocking group covalently attached thereto, such that the 3′ carbon atom has attached a group of the structure —O-Z wherein Z is any of —C(R′)2-O—R″, —C(R′)2-N(R″)2, —C(R′)2-N(H)R″, —C(R′)2-S—R″ and —C(R′)2-F, wherein each R″ is or is part of a removable protecting group; each R′ is independently a hydrogen atom, an alkyl, substituted alkyl, arylalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclic, acyl, cyano, alkoxy, aryloxy, heteroaryloxy or amido group, or a detectable label attached through a linking group; or (R′)2 represents an alkylidene group of formula ═C(R′″)2 wherein each R′″ may be the same or different and is selected from the group comprising hydrogen and halogen atoms and alkyl groups; and wherein said molecule may be reacted to yield an intermediate in which each R″ is exchanged for H or, where Z is —C(R′)2-F, the F is exchanged for OH, SH or NH2, preferably OH, which intermediate dissociates under aqueous conditions to afford a molecule with a free 3′OH; with the proviso that where Z is —C(R′)2-S—R″, both R′ groups are not H.
-
Citations
18 Claims
-
1. A modified nucleotide molecule comprising a purine or pyrimidine base and a ribose or deoxyribose sugar moiety having a removable 3′
- -OH blocking group covalently attached thereto, such that the 3′
carbon atom has attached a group of the structure
—
O-Zwherein Z is any of —
C(RIV)2—
O—
R″
, —
C(R′
)2—
N(R″
)2, —
C(R′
)2—
N(H)R″
, —
C(RIV)2—
S—
R″ and
—
C(R′
)2—
N3,wherein —
C(RIV)2—
O—
R″
is of the formula —
CR4(R5)—
O—
CR4(R5)—
OR6 or of the formula —
CR4(R5)—
O—
CR4(R5)—
SR6; and
wherein —
C(RIV)2—
S—
R″
is of the formula —
CR4(R5)—
S—
CR4(R5)—
OR6 or of the formula —
CR4(R5)—
S—
CR4(R5)—
SR6;wherein each R″
is or is part of a removable protecting group;each R′
is independently a hydrogen atom, an alkyl, substituted alkyl, arylalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclic, acyl, cyano, alkoxy, aryloxy, heteroaryloxy or amido group, or a detectable label attached through a linking group;
or (R′
)2 represents an alkylidene group of formula ═
C(R′
″
)2 wherein each R′
″
may be the same or different and is selected from the group comprising hydrogen and halogen atoms and alkyl groups;each R4 and R5 is independently a hydrogen atom or an alkyl group; R6 is alkyl, cycloalkyl, alkenyl, cycloalkenyl or benzyl; and wherein said molecule may be reacted to yield an intermediate in which each R″
is exchanged for H, which intermediate dissociates under aqueous conditions to afford a molecule with a free 3′
OH;
with the proviso that where Z is —
C(RIV)2—
S—
R″
, both RIV groups are not H. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
- -OH blocking group covalently attached thereto, such that the 3′
Specification