Intermediates for providing functional groups on the 5' end of o

Details Intermediates for providing functional groups on the 5' end of o Intermediates for providing functional groups on the 5' end of o

1992-07-15

1995-02-21

Rollins, John W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Acyclic carbon bonded directly to three benzene rings or to...

536 2532, 549214, 549388, C07B 3900

Patent

active

053917855

ABSTRACT:
Phosphoramidites of the formula ##STR1## where R is a base-labile protecting group, R.sup.1 and R.sup.2 are individually alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, or aryl of 6 to 20 carbon atoms or are joined together to form with the nitrogen atom a cyclic structure of 4-7 carbon atoms and 0 to 1 annular chalcogen atoms of atomic number 8 to 16, G is a hydrocarbylene group of 1 to 20 carbon atoms and Z is a hydroxy-protected vicinal diol group bound to G by one of the vicinal diol carbon atoms or a disulfide group and bound to G by one of the sulfur atoms of the disulfide group, with the proviso that G is of at least 4 carbon atoms when Z is said disulfide group are used in conventional automated oligonucleotide synthesis to introduce a functional aldehyde or thiol group on the 5' end of the oligonucleotide to thereby provide a reactive site on the oligonucleotide that may be used to conjugate the oligonucleotide to molecules that contain a free amino group or an electrophilic center reactive with a thiol group.

REFERENCES:
patent: T909012 (1973-04-01), McCollum
patent: 2028403 (1936-01-01), Mares
patent: 2362326 (1944-11-01), Thurston et al.
patent: 2585884 (1952-02-01), Whetstone et al.
patent: 2619493 (1952-11-01), Norris
patent: 2946806 (1960-07-01), Nentwig et al.
patent: 3004894 (1961-10-01), Johnson et al.
patent: 3201420 (1965-08-01), Fuzesi et al.
patent: 3225063 (1965-12-01), D'Alelio
patent: 3308064 (1967-03-01), Schlight et al.
patent: 3926912 (1975-12-01), Mayer-Mader et al.
patent: 4058550 (1977-11-01), Shepard et al.
patent: 4191668 (1980-03-01), Katz
patent: 4220565 (1980-09-01), Katz
patent: 4465869 (1984-08-01), Takaishi et al.
patent: 4575558 (1986-03-01), Mai et al.
patent: 4588824 (1986-05-01), Baldwin et al.
patent: 4650675 (1987-03-01), Borel et al.
patent: 4751181 (1988-06-01), Keene
patent: 4845219 (1989-07-01), Inoue et al.
patent: 4877891 (1989-10-01), Becker et al.
patent: 4983759 (1991-01-01), Inoue et al.
patent: 4997928 (1991-03-01), Hobbs
patent: 5252760 (1993-10-01), Urdea et al.
IMitsuo et al., "Preparation of lecithin-type of phospholipid analogues and mesomorphic states" Chem. Pharm. Bull. (1978) 26(5):1493-1500.
Gupta et al., "A general method for the synthesis of 3'-sulfhydryl and phosphate group containing oligonucleotides" Chem. Abstracts (1991) 115:976 (abstract No. 183758p).
Agrawal S., et al., Nucl. Acids Res. (1986) 14(15):6227-6245.
Kremsky J., et al., Nucl. Acids Res. (1987) 15(7):2891-2909.
Eshhar Z., et al., J. Immunol. (1975) 114(2):872-876.
Borel Y., et al., Science (1973) 182:76-78.
Parker L., et al., J. Immunol. (1974) 113(1):292-297.
Borel H., et al., Ann. N.Y. Acad. Sci. (1986) 475:296-306.
Papalian M., et al., J. Clin. Invest. (1980) 65:469-477.
Stollar B., et al., J. Clin. Invest. (1980) 66:210-219.
Borel Y., et al., J. Clin. Invest. (1988) 82:1901-1907.
Williams et al., "Stereocontrolled Transformations of Orthoester Intermediates into Substituted Tetrahydrofurans," J. Am. Chem. Soc., 106(9), 2641-2644 (1984).
Verkade et al., "Synthesen von Glyceriden mit Hilfe von Tritylverbindungen. IV.," Recl. Trav. Pays-Bas, 59, 1123-1140 (1940).
Baggett et al., "Aspects of Stereochemistry. Part XXI. Absolute Configuration of Benzylidene Derivatives of Some Acyclic Polyhydric Alcohols," J. Chem. Soc., 1965, 3394-3400 .
Jackson et al., "Synthetic Glycerides. IV. Esters of Aromatic and Aliphatic Acids," J. Am. Chem. Soc., 55, 678-680 (1933).
Frechet et al., "Use of Polymers as Protecting Groups in Organic Synthesis. III. Selective Functionalization of Polyhydroxy Alcohols," Can. J. Chem., 54, 926-934 (1976).
Ichikawa et al., "An Asymmetric Synthesis of Glycerol Derivatives by the Enantioselective Acylation of Prochiral Glycerol," Chem. Lett., 1984, 949-952.
Sedarevich, "Glyceride Isomerizations in Lipid Chemistry," J. Am. Oil Chem. Soc., 44(7), 381-=393 (1967); Chem. Abstr., 67, p. 10965, Abstr. No. 116524m (1967), Only abstract supplied.
Shvets et al., "Lipids. LIX. Determination of the Configuration of a, .beta.-Diglycerides Prepared from D-Mannitol," Zh. Org. Kihm., 4(4), 597-603 (1968); Chem. Abstr., 69, p. 231, Abstr. No. 2454z, (1968); Only abstract supplied.
Hedgley et al., "Glycerol Esters of Thiobenzoic O-Acids and Thioglycerol Esters of Benzoic Acid," J. Chem. Soc. C, 1970, 467-471.
Barker et al., "Herbicidal (Benzyloxy)dioxanes and [(Benzyloxy)methyl]dioxolanes," Ger. Offen. 2,326,586, 06 Dec. 1973; Chem. Abstr., 80, p. 360, Abstr. No. 59946t (1974); Only abstract supplied.

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