Compounds, compositions, and methods for isolation of nucleic acids

A method of isolating a nucleic acid from a sample, comprising:

• (a) providing a sample containing a nucleic acid;
• (b) contacting the sample with a composition comprising:
• a solid surface;
• a linker covalently attached to the solid surface, wherein the linker has a structure:
• —(CH2)n1—Z—(CH2)n2—
• wherein n1 and n2 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8, and Z is selected from —NHC(O)NH—, —C(O)NH—, —OC(O)NH—, —OC(O)O—, —NHC(O)S—, —NHC(S)NH—, —O—, and —C(O)O—;
• and
• a moiety of formula (I) covalently attached to the linker:
• wherein:
• X is selected from O, S, S(O), and S(O)2;
• and
• R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, aryl, heteroaryl, heterocyclyl, halo, cyano, nitro, —ORa, —SRb, —C(O)ORc, —C(O)NRdRe, —OC(O)NRfRg, —NRhC(O)NRiRj, and —NRhC(S)NRiRj, wherein each Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, and Rj is independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, and aryl;
• at a pH of less than about 8.0, wherein the nucleic acid binds to the composition to provide a nucleic acid bound composition;
• and
• (c) separating the nucleic acid bound composition from the sample.

A compound of formula (IIa):

• or a salt thereof, wherein:
• X is selected from O, S, S(O), and S(O)2;
• L is a linker, wherein the linker has a structure:
• —(CH2)n1—Z—(CH2)n2—
• wherein n1 and n2 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8, and Z is selected from —NHC(O)NH—, —C(O)NH—, —OC(O)NH—, —OC(O)O—, —NHC(O)S—, —NHC(S) NH—, —O—, and —C(O)O—;
• each Ra is independently selected from hydroxy, C1-C6 alkoxy, and halo;
• and
• R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, aryl, heteroaryl, heterocyclyl, halo, cyano, nitro, —ORa, —SRb, —C(O)ORc, —C(O)NRdRe, —OC(O)NRfRg, NRhC(O)NRiRj, and —NRhC(S)NRiRj, wherein each Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, and Rj is independently selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, and aryl.