106568-79-0Relevant academic research and scientific papers
Preparation of oligodeoxynucleotides containing 6-methylthiopurine residues by chemical synthesis or specific methylation
Xu,Zheng,Swann
, p. 929 - 933 (1995)
Two methods (chemical synthesis and specific methylation) are described for the preparation of oligodeoxynucleotides containing 6-methylthiopurine residues. 6-Methylthiopurine phosphoramidite (6) is prepared and incorporated into oligomers. Methylation with methyl iodide of 6-thiopurine (or 6-thioguanine) in oligonucleotides also leads to exclusive production of 6-methylthiopurine (or 6-methylthioguanine) oligomers.
TEMPO-derived spin labels linked to the nucleobases adenine and cytosine for probing local structural perturbations in DNA by EPR spectroscopy
Gophane, Dnyaneshwar B.,Sigurdsson, Snorri Th.
, p. 219 - 227 (2015)
Three 2'-deoxynucleosides containing semi-flexible spin labels, namely TA, UA and UC, were prepared and incorporated into deoxyoligonucleotides using the phosphoramidite method. All three nucleosides contain 2,2,6,6-tetram
Nucleophile-catalyzed additions to activated triple bonds. protection of lactams, imides, and nucleosides with MocVinyl and related groups
Mola, Laura,Font, Joan,Bosch, Lluis,Caner, Joaquim,Costa, Anna M.,Etxebarria-Jardi, Gorka,Pineda, Oriol,De Vicente, David,Vilarrasa, Jaume
, p. 5832 - 5842 (2013/07/26)
Additions of lactams, imides, (S)-4-benzyl-1,3-oxazolidin-2-one, 2-pyridone, pyrimidine-2,4-diones (AZT derivatives), or inosines to the electron-deficient triple bonds of methyl propynoate, tert-butyl propynoate, 3-butyn-2-one, N-propynoylmorpholine, or
Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6-halo- and 2,6-dihalopurine nucleosides and 2′-deoxynucleosides with acyl or silyl halides
Francom, Paula,Robins, Morris J.
, p. 666 - 669 (2007/10/03)
Treatment of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine (1) with TMS-Cl and benzyltriethylammonium nitrite (BTEA-NO2) in dichloromethane gave the crystalline 2,6-dichloropurine nucleoside 2, and acetyl chloride/BTEA-NO2 was equally effective (～85%, without chromatography). TMS-Br/tert-butyl nitrite/dibromomethane gave crystalline 2-bromo-6-chloro analogue 3 (85%). (Chloro or bromo)-dediazoniation of 3′,5′-di-O-acetyl-2′-deoxyadenosine (4) gave the 6-[chloro (5, 63%) or bromo (6, 80%)]purine deoxynucleosides, and 2′,3′,5′-tri-O-acetyladenosine (8) was converted into the 6-chloropurine nucleoside 9 (71%).
An efficient method for the synthesis of [4-15N]cytidine, 2'-deoxy[4-15N]cytidine, [6-15N]adenosine, and 2'-deoxy[6-15N]adenosine derivatives
Kamaike,Takahashi,Utsugi,Tomizuka,Okazaki,Tamada,Kinoshita,Masuda,Ishido
, p. 749 - 769 (2007/10/03)
Nucleophilic substitution reactions of 4-azolyl-1-β-D-ribofuranosylpyrimidin-2(1H)-one and 6-azolyl-9-β-D-ribofuranosyl-9H-purine derivatives, which were converted from uridine and inosine, with [15N]phthalimide in the presence of triethylamine
Synthesis and duplex stability of oligodeoxynucleotides containing 6-mercaptopurine
Xu, Yao-Zhong,Zheng, Qinguo,Swann, Peter F.
, p. 5837 - 5840 (2007/10/02)
simple procedures for conversion of 2′-deoxyinosine into 6-thio-2′-deoxyinosine (III) and for preparation of S-protected 6-mercatopurine phosphoramidite (VI) are described. The monomer (VI) was incorporated into DNA oligomers and converted into oligomers containing 6-mercaptopurine and other purines modified at the 6-position. Measurements of the melting temperature (Tm) of DNA duplexes containing 6-mercaptopurine or 6-thioguanine show that both preferentially pair with cystosine rather than with thymine, but that the presence of the S generally destabilises the DNA duplex.
