25 research outputs found
Synthesis of protected guanidinium linked dinucleoside incorporable into an oligonucleotide using solid phase DNA methodology
No full textThe synthesis of novel fully protected guanidinium linked dinucleoside for incorporation into oligonucleotide using solid-phase DNA synthesis methodology was developed. The three different protecting groups selected allow different deprotection conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.PT: J; CR: BARAWKAR DA, 1996, NUCLEIC ACIDS RES, V24, P1229 BLASKO A, 1996, J AM CHEM SOC, V118, P7892 BLASKO A, 1997, BIOCHEMISTRY-US, V36, P7821 COOK PD, 1991, ANTI-CANCER DRUG DES, V6, P585 DEMESMAEKER A, 1995, ACCOUNTS CHEM RES, V28, P366 DEMESMAEKER A, 1996, ANGEW CHEM INT EDIT, V35, P2790 DEMPCY RO, 1995, J AM CHEM SOC, V117, P6140 DEMPCY RO, 1996, P NATL ACAD SCI USA, V93, P4326 FATHI R, 1994, NUCLEIC ACIDS RES, V22, P5416 GRYAZNOV SM, 1997, NUCLEOS NUCLEOT, V16, P899 HASHIMOTO H, 1993, J AM CHEM SOC, V115, P7128 HAYAKAWA Y, 1986, J ORG CHEM, V51, P2400 JONES RJ, 1993, J ORG CHEM, V58, P2983 JUST G, 1976, SYNTHESIS-STUTTGART, P457 KEAN JM, 1995, BIOCHEMISTRY-US, V34, P14617 LETSINGER RL, 1988, J AM CHEM SOC, V110, P4470 LINKLETTER B, 1998, IN PRESS BIOORG MED MILLIGAN JF, 1993, J MED CHEM, V36, P1923 NIELSEN PE, 1991, SCIENCE, V254, P1497 PANNECOUQUE C, 1992, TETRAHEDRON LETT, V33, P7609 RICE JS, 1997, BIOCHEMISTRY-US, V36, P399 ROBINSON S, 1997, TETRAHEDRON, V53, P6697 SANGHVI YS, 1993, NUCLEOS NUCLEOT, P311 SANGHVI YS, 1997, NUCLEOS NUCLEOT, V16, P907 SCHMID N, 1995, TETRAHEDRON LETT, V36, P1447 UHLMANN E, 1990, CHEM REV, V90, P543 VANDENDRIESSCHE F, 1993, J CHEM SOC P1, P1567; NR: 27; TC: 18; J9: BIOORG MEDICINAL CHEM LETTER; PG: 4; GA: ZV310Source type: Electronic(1
Solid phase synthesis of DNA containing 5-NH2-2′-deoxyuridine
No full textSolid phase synthesis of DNA containing 5-amino-2'-deoxyuridine is reported using trifluoroacetyl as a 5-NH2 protector
Fluorescent d (CGCGAATTCGCG): characterization of major groove polarity and study of minor groove interactions through a major groove semantophore conjugate
No full textThe major and minor groove in duplex DNA are sites of specific molecular recognition by DNA-binding agents such as proteins, drugs and metal complexes and have functional significance. In view of this, understanding of the inherent differences in their environment and the allosteric information transfer between them induced by DNA-binding agents assumes importance. Site-specific incorporation of 5-aminodansyl-dU, (U) in oligonucleotides d(CGCGAAUTCGCG) and d(CGCGAATUCGCG) leads to fluorogenic nucleic acids, in which the reporter group resides in the major groove. The fluorescent observables from such a probe are used to estimate the dielectric constant of the major groove to be -55D, in comparison to the reported non polar environment of the minor groove (-20D) in poly d[AT]-poly d[AT]. An exclusive minor groove event such as DNA-netropsin association can be quantitatively monitored by fluorescence of the dansyl moiety located in the major groove. This suggests existence of an information network among the two grooves. The fluorescent DNA probes as reported here may have potential applications in the study of structural polymorphisms in DNA, DNA ligand interactions and triple helix structure
Molecular recognition of 5-amino-dU in the central strand of a DNA triplex: formation of triads A<SUP>∗</SUP>U#:A in parallel and G<SUP>∗</SUP>U#:A in antiparallel motif
No full textThis article does not have an abstract
Synthesis of protected guanidinium linked dinucleoside incorporable into an oligonucleotide using solid phase DNA methodology
No full textSynthesis of site-specific oligonucleotide-polyamine conjugates
No full textSynthesis of 5-Me-dC-amidite regiospecifically tethered at C4, with triethylenetetramine (8) and spermine (9) and their site specific incorporation into DNA to obtain oligonucleotide-polyamine conjugates (10-15) is reported
Polarity sensing by fluorescent oligonucleotides: first demonstration of sequence-dependent microenvironmental changes in the DNA major groove
No full textDNA duplex recognition by macromolecules (proteins, enzymes) and small molecules (drugs, metal complexes) occurs in the major or minor grooves of DNA via hydrogen bonding and electrostatic or hydrophobic interactions, whose strengths depend on the medium. It is therefore important to understand the local environments of the major/minor grooves of DNA. It is known that small molecules bind in the minor groove that have nonpolar character (ε = 22) and are organic-like. By employing fluorescent oligonucleotides, we demonstrated recently that the major groove of DNA is more polar than the minor groove (ε = 55) and the DNA double helix has different polarity in its two grooves. Our experimentally measured values were recently validated independently by two theoretical groups, employing calculations by two different methodologies. In this paper, a hitherto unknown property of DNA double helix ¯ sequence dependent local polarity or microenvironment - is experimentally demonstrated. This is shown by fluorescence experiments using oligonucleotides containing the modified base 5-amino-dU in place of dT and the polarity varied between ε ≈ 40 and 60, in different sequences. This is the first experimental demonstration of sequence-dependent microenvironmental effects in DNA in solution, although structural effects are well-known by X-ray data. The technique used has a good potential to investigate differing microenvoronmental effects in various secondary structures, DNA polymorphs, and chemically modified DNA and their hybrids
Effect of C5-amino substituent on 2'-deoxyuridine base pairing with 2'-deoxyadenosine: investigation by <SUP>1</SUP>H and <SUP>13</SUP>C NMR spectroscopy
No full textSubstituents at 5-position of a pyrimidine base are known to affect its base pairing properties with complementary purines, either by altering the imino N3-H acidity or by modifying the acceptor strength of C2 and C4 carbonyls. This paper reports comparative base pair property of 5-methyl-2'-deoxyuridine (dT) and 5-amino-2'-deoxyuridine (dUNH2) with 2'-deoxyadenosine (dA) as their 3',5'-di-t-butyldimethylsilyl derivatives in chloroform-d. Using 1H and 13C NMR, it is demonstrated that the 5-NH2 substituent in 2'-deoxyuridine results in (i) decreased association (lower Ka) with 2'-deoxyadenosine compared to dA:dT complexation and (ii) increased receptor strength of C2 carbonyl compared to C4 carbonyl and (iii) lower temperature for separation of 6-amino protons of dA due to its complexation with dUNH2 compared to that with dT
Deoxynucleic Guanidines/PNA (DNG/PNA) Chimeras: Oligonucleoside Analogue Containing Cationic Guanidinium and Neutral Amide Linkages
No full textDeoxynucleic Guanidines/PNA (DNG/PNA)
Chimeras: Oligonucleoside Analogue Containing
Cationic Guanidinium and Neutral Amide Linkage
