Nucleosides and oligonucleotides with diynyl side chains: The Huisgen-Sharpless cycloaddition "click reaction" performed on dna and their constituents

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 6-7, 2007, Pages 597-601

  Seela, Frank ^a,b   Sirivolu, Venkata Ramana ^c  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c NONE

Author keywords

Dipropargyl ether; Huisgen Sharpless cycloaddition; Nucleosides; Octadiynyl; Phosphoramidites

Indexed keywords

DIPROPARGYL ETHER; NUCLEOSIDE; OCTADINYL; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; CYCLOADDITION; DNA STRUCTURE; DNA SYNTHESIS; STRUCTURE ACTIVITY RELATION;

CHEMISTRY, ORGANIC; DNA; ENEDIYNES; MODELS, CHEMICAL; NUCLEOSIDES; OLIGONUCLEOTIDES; TRANSITION TEMPERATURE;

EID: 36949030225     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701490308     Document Type: Conference Paper

References (6)

1. Sági, J.; Szemzö, A.; Ébinger, K.; Szabolcs, A.; Sági, G.; Ruff, E.; Ötvös, L. Base-modified oligodeoxynucleotides. I. Effect of 5-alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines on duplex stability and hydrophobicity. Tetrahedron Lett. 1993, 34, 2191-2194.
2. Seela, F.; Zulauf, M. Oligonucleotides containing 7-deazaadenines: The influence of the 7-substituent chain length and charge on the duplex stability. Helv. Chim. Acta 1999, 82, 1878-1898.
3. Seela, F.; Sirivolu, V.R. DNA containing side chains with terminal triple bonds: Base-pair stability and functionalization of alkynylated pyrimidines and 7-deazapurines.Chem. Biodiv. 2006, 3, 509-514.
4. 6)DMSO): 3.47 (s, 1 H, C≡CH); 6.10 (t, H-C(1)′); 8.26 (s , H-C(6));11.63 (s, NH).
5. 3): 150.19, 149.65.
6. Seela, F.; Feiling, E.; Gross, J.; Hillenkamp, F.; Ramzaeva, N.; Rosemeyer, H.; Zulauf, M. Fluorescent DNA: The development of 7-deazapurine nucleoside triphosphates applicable for sequencing at the single molecule level. J. Biotechnol. 2001, 86, 269-279.