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Polynucleotide reagents containing modified deoxyribose moieties, and associated methods of synthesis and use

  • US 5,597,909 A
  • Filed: 08/25/1994
  • Issued: 01/28/1997
  • Est. Priority Date: 08/25/1994
  • Status: Expired due to Fees
First Claim
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1. A reagent having the structural formula ##STR12## wherein:

  • R1 is selected from the group consisting of hydrogen, acid-sensitive, base-stable protecting groups and acyl capping groups;

    R2 is a phosphorus derivative selected to enable addition of the reagent to a molecular species containing a free hydroxyl group, or is a linkage to a solid support;

    R3 is selected from the group consisting of hydrogen, hydroxyl, sulfhydryl, halogeno, amino, alkyl, allyl, -OR6 wherein R6 is alkyl, allyl, silyl or phosphate;

    R4 is either hydrogen or -(CH2)m OR7 wherein R7 is alkyl or -(CO)R8, R8 is alkyl and m is an integer in the range of 0 to 12 inclusive;

    R5 is -A-Z-X(R9)n;

    A is oxygen, sulfur or methylene;

    Z is arylene, C6 -C18 aralkylene or C1 -C12 alkylene containing 0 to 6 heteroatoms selected from the group consisting of O, S, N, Si and Se and 0 to 6 linkages selected from the group consisting of -CO-, -COO-, -CONH-, -NHCO-, -S-S-, -SO2 -, -CH(OH)-CH(OH)-, -CH(OR15)-CH(OR15)-,-O-PO(O31 )-O-, -O-P)(R15)-, -O-P)(OR15)-O-, -O-P)(OR15)-R16 - and -PO(OR15)-O-R16 - in which R15 is lower alkyl and R16 is lower alkylene, and, if Z is aralkylene or alkylene, containing 0 to 3 unsaturated bonds;

    X is selected from the group consisting of -NH-, -CONH-, -NHCO-, -CO-, -S- and -Si≡

    ;

    R9 is hydrogen, a protecting group, a detectable label, or, unless X is -Si≡

    , a solid support; and

    n is 1 when X is -NH-, -CONH-, -NHCO-, -CO-, or -S-, and is 3 when X is -Si≡

    ,with the proviso that if R2 represents a linkage to a solid support, R9 is hydrogen, a protecting group, or a detectable label.

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