75794-55-7Relevant academic research and scientific papers
Guanine specific DNA cleavage by photoirradiation of dibenzoyldiazomethane - Oligonucleotide conjugates
Nakatani, Kazuhiko,Shirai, Junya,Sando, Shinsuke,Saito, Isao
, p. 7626 - 7635 (1997)
Photoirradiation of dibenzoyldiazomethane (DBDM) produced highly electrophilic benzoylketene via Wolff rearrangement. DBDM derivative possessing an aminoalkyl side chain induced a DNA cleavage selectively at guanine (G) residues upon photoirradiation and subsequent piperidine treatment. In order to devise photochemical DNA cleavers that can specifically alkylate a guanine residue proximal to the target sequence of long DNA fragments, a sew reagent, DBDM-OSu, which facilitates the connection of DBDM unit to various DNA binders, was developed. DBDM-oligonucleotide (ODN) conjugates 5 and 6 were obtained by the coupling of 5'-aminohexyl 8-mer [H2N-CH2)6-d(ACGTCAGG)-3'] and 15-mer [H2N-(CH2)6-d(ACGTCAGGTGGCACT)-3'], respectively, with DBDM-OSu in aqueous acetonitrile in the presence of sodium bicarbonate. Photoirradiation of 5 and 6 in the presence of 25-mer 5'-d(AGTGCCACCTGACGTCTG18CTCTCTC)-3' having a complementary sequence induced cross-linking of both oligomers. A distinct cleavage band at guanine residue (G18) was observed upon heating the cross-linked oligomers with piperidine. A similar DNA cleavage reaction of 5'-d(AGTGCCACCTGACG14TG16CG18TG20CG22-TCT)-3' having multiple guanine sites in the presence of DBDM-ODN conjugate 6 indicated that the most effectively cleaved site is G16. These results demonstrated that DBDM-oligonucleotide conjugates can serve as a new class of photonucleases that can cleave single-stranded DNA at predetermined guanine sites. Furthermore, the reagent DBDM-OSu can be used as a convenient and effective photoinducible electrophile for the cross-linking or the modification of biopolymers.
Electronic and spectroscopic properties of avobenzone derivatives attached to Mo2 quadruple bonds: Suppression of the photochemical enol-to-keto transformation
Chisholm, Malcolm H.,Durr, Christopher B.,Gustafson, Terry L.,Kender, William T.,Spilker, Thomas F.,Young, Philip J.
, p. 5155 - 5162 (2015)
From the reactions between Mo2(TiPB)4, where TiPB is 2,4,6-triisopropylbenzoate, and 2 equiv of the acids 4-formylbenzoic acid, HBzald; 4-(3-oxo-3-phenylpropanoyl)benzoic acid, HAvo; and 4-(2,2-difluoro-6-phenyl
Photogeneration of Highly Electrophilic Benzoylketene from Dibenzoyldiazomethane in Aqueous Solvents: Reaction with Amino Acids and DNA Cleavage
Nakatani, Kazuhiko,Shirai, Junya,Tamaki, Ryo,Saito, Isao
, p. 5363 - 5366 (2007/10/02)
Photoirradiation of dibenzoyldiazomethane in the presence of amino acid derivatives in aqueous solutions efficiently produced the addition products through a reaction with photogenerated benzoylketene.Efficient DNA cleavage was observed with a dibenzoyldiazomethane derivative, possessing a cationic side chain under photoirradiation conditions.
