Reagents for the preparation of 5'-biotinylated oligonucleotides

Claim 2

A chemical compound of the formula Bt-(SG)-A-Q wherein Bt is ##STR23## SG is an organic diradical spacer group that separates Bt from A at a distance sufficient to allow efficient complexation of Bt to avidin or streptavidin; A is selected from the group consisting of --O--, --S--, ##STR24## wherein R and R 1 are independently selected from the group consisting of H, C 3-10 branched alkyl, C 1-10 unbranched alkyl, C 6-10 aryl, C 7-12 alkaryl, and C 7-12 aralkyl; Q is selected from the group consisting of ##STR25## and salts thereof; wherein R 2 and R 3 are independently selected from the group consisting of C 3-10 branched alkyl and C 1-12 unbranched alkyl; R 4 is selected from the group consisting of --(CRR 1 ) m (A) n (CRR 1 )m--, ##STR26## R, R 1 and A are as defined above; m=1-6; n=0-1; p=1-10; q=0-10, provided that 2m+n≦ 12, and further provided that 2≦n+p+q≦13; and Y is any phosphate-protecting group.

Claim 3

A compound according to claim 1 wherein SG is --(CH 2 ) r --X--; r=2-3; X is selected from the group consisting of --CH 2 --, --X 1 L--, and ##STR27## X 1 is selected from the group consisting of --CH 2 O--, --CH 2 S--, ##STR28## R and R 1 are as defined above; and R 5 is selected from the group consisting of ##STR29## and alkyl-substituted derivatives thereof; t=0-10; and L is selected from the group consisting of substituted and unsubstituted derivatives selected from the group consisting of C 2-20 alkylene wherein the alkylene segment may contain one or more groups selected from the group consisting of arylene, cycloalkylene, heterocyclene, ether, thioether, sulfone, sulfoxide, amide, ureido, keto, and dithio; C 3-8 cycloalkylene; C 4-20 . alkylenecycloalkyl; C 6-10 arylene; ##STR30## wherein z=1-10; C 7-20 arylalkylene; and 3-10 membered ring aromatic or alicyclic heterocyclenes wherein the heteroatom(s) may be selected from the group Consisting of N, O, and S.

Claim 4

A compound according to claim 2 wherein r is 2, X is --CH 2 --, and A is --CH 2 --.

Claim 5

A compound according to claim 2 wherein r is 3.

Claim 6

A compound according to claim 4 wherein X is --CH 2 --.

Claim 7

A compound according to claim 4 wherein A is --O--.

Claim 8

A compound according to claim 6 wherein X is --CH 2 --.

Claim 9

A compound according to claim 6 wherein X is ##STR31##

Claim 10

A compound according to claim 6 wherein X is --X 1 --L--, X 1 is ##STR32## and R is selected from the group consisting of H, C 1-4 unbranched alkyl, and C 3-5 branched alkyl.

Claim 11

A compound according to claim 9 wherein R is selected from the group consisting of H and CH 3 .

Claim 12

A compound according to claims 3, 5, 7, 8, or 10 wherein Q is selected from the group consisting of ##STR33##

Claim 13

A compound according to claim 11 wherein Y is selected from the group consisting of 4--Cl--C 6 H 4 --O--; 2--Cl--C 6 H 4 --O--; 4--NO 2 --C 6 H 4 --O--; 4--NO 2 --C 6 H 4 CH 2 CH 2 l --O--; 2,4--NO 2 --C 6 H 3 CH 2 CH 2--O--; 2,4-Cl 2 --C 6 H 3 --O--; 2,3-Cl 2 --C 6 H 3 --O--; NCCH 2 CH 2 O--; NCCH 2 C(CH 3 ) 2 --O--; CH 3 O--; (Z) 3 CCH 2 --O--; (Z) 3 CC(CH 3 ) 2 --O--R'S--; R'SCH 2 CH 2 --O--; R'SO 2 CH 2 CH 2 --O--; and R'NH--, wherein Z is selected from the group consisting of Cl, Br, and I, and R' is selected from the group consisting of H, C 3-1 branched alkyl, C 1-10 unbranched alkyl, C 6-10 aryl, C 7-12 alkaryl, and C 7-12 aralkyl.

Claim 14

A compound according to claim 12 wherein Q is ##STR34## and R 2 and R 3 are --CH(CH 3 ) 2 .

Claim 15

A compound according to claim 13 wherein Y is selected from the group consisting of NCCH 2 CH 2 O-- and CH 3 O--.

Claim 16

A compound according to claim 14 wherein R is H and L is C 2-20 alkylene.

Claim 17

A compound according to claim 15 wherein L is selected from the group consisting of --(CH 2 ) 2 -- and --(CH 2 ) 3 --.

Claim 18

A compound according to claim 14 wherein R is H and L is 1,4-cyclohexylene.

Claim 19

A compound according to claim 14 wherein R is H, L is ##STR35## and v=1-10.

Claim 20

A compound according to claim 18 wherein L is ##STR36##

Claim 21

A compound according to claim 14 wherein R is H,L is ##STR37## v is 1-10 and w is 1-10.