An Infrared Study of Hydrogen Bonding between Adenine and Uracil Derivatives in Chloroform Solution

Kyogoku, Yoshimasa; Lord, R. C.; Rich, Alexander

doi:10.1021/ja00979a005

Cited by 286 publications

(173 citation statements)

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“…This conclusion was received with some skepticism at the time. Dr. Y. Kyogoku, working with Professors Richard Lord and Alex Rich at MIT, had independently shown by infrared spectroscopy that derivatives of A and T, and G and C, formed horizontal complementary base pairs in CHCl 3 , just as predicted by Watson and Crick for doublehelical DNA (52,53). It soon became clear that the difference in solvent, water in the case of the NMR experiments and CHCl 3 in the case of the infrared experiments, accounted for the differences in the solution behavior of these molecules.…”

Section: My First Research Program In Biophysics: Base-stacking Of Numentioning

confidence: 98%

A Physical Chemist's Expedition to Explore the World of Membrane Proteins

Chan

2009

Annu. Rev. Biophys.

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NMR of base-stacking interactions in nucleic acids in solution, dynamic structure of bilayer membranes, membrane biophysics, metal cofactor structure and function, redox linkage and proton pumping in cytochrome c oxidase, methane hydroxylation by the particulate methane monooxygenase, early kinetic events in protein folding AbstractDespite growing up amid humble surroundings, I ended up receiving an excellent education at the University of California at Berkeley and postdoctoral training at Harvard. My academic career at Caltech was shaped by serendipity, inspirational colleagues, and a stimulating research environment, as well as smart, motivated students and postdocs who were willing to join my search for molecular understanding of complex biological systems. From chemical physics I allowed my research to evolve, beginning with the application of NMR to investigate the base stacking of nucleic acid bases in solution, the dynamic structure of membranes, and culminating with the use of various forms of spectroscopy to elucidate the structure and function of membrane proteins and the early kinetic events in protein folding. The journey was a biased random walk driven by my own intellectual curiosity and instincts and by the pace at which I learned biochemistry from my students and postdocs, my colleagues, and the literature and through osmosis during seminars and scientific meetings.

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Section: My First Research Program In Biophysics: Base-stacking Of Numentioning

confidence: 98%

A Physical Chemist's Expedition to Explore the World of Membrane Proteins

Chan

2009

Annu. Rev. Biophys.

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“…振动峰 [20] 以及聚合物中腺嘌呤上伯胺 N-H 变形振动峰 [21] . 谱线 c 中, 1724 和 1672 cm -1 分别为 5-氟尿嘧啶中 C(2)＝O 和 C(4)＝O 伸缩振动峰 [20] .…”

Section: 实验过程unclassified

“…振动峰 [20] 以及聚合物中腺嘌呤上伯胺 N-H 变形振动峰 [21] . 谱线 c 中, 1724 和 1672 cm -1 分别为 5-氟尿嘧啶中 C(2)＝O 和 C(4)＝O 伸缩振动峰 [20] . 与 a, c 对比可知, 在 Figure 3 FT-IR spectra of (a) PCASE polymer, (b) PCASE/5-flu nanospheres and (c) 5-fluorouracil in 1780～1580 cm …”

Section: 实验过程unclassified

Preparation and Properties of Amphiphilic Polymer Nanospheres Containing Aza-crown ether

Zhang¹,

Xie²,

Zhang³

et al. 2012

Acta Chim. Sinica

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An amphiphilic polymer containing adenine and aza-crown ethers, poly-{[N,N-bis(2-ethoxy)-1,10-diaza-18-crown-6][5-methylene-(1-adenine)]sophthaloyl ester} (PCASE), was synthesized. The SEM morphology observed indicates that the amphiphilic PCASE polymer self-organized into diameters of about 140～210 nm nanospheres in dilute aqueous solution after recognized with 5-fluorouracil spontaneously. The sizes of PCASE/5-flu nanospheres in dilute aqueous solution determined by dynamic light scattering (DLS) are mainly dispersed at 120～230 nm. The molecule recognition based on hydrogen bond between adenine of polymer and 5-fluorouracil substrate in PCASE/5-flu nanospheres was studied. After recognition the C(2)＝O stretching vibration at 1724 cm -1 of 5-fluorouracil subtract shifted to 1718 cm -1 , the NH 2 stretching vibration at 3324 cm -1 disappeared, and a new peak at 3432 cm -1 arised, indicating the formation of hydrogen bonds between 5-fluorouracil and adenine in polymer PCASE． The study on variable temperature FTIR show that the peak 1718 cm -1 gradually shifted back to the position at 1724 cm -1 , and the new peak 3432 cm -1 disappeared finally, indicating that the H-bond was broken.

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“…In DNA and the polynucleotides investigated, one NH group of the -NH, groups is free, that is, not linked by a hydrogen bond. Kyogoku et al (6) as well as Miller and Sobell (7) investigated model substances such as 9-methyl-and 9-ethyladenine in CDCl,. Here they find bands at 3517 and 3416 cm-I in diluted solutions and assign these to, respectively, the antisymmetric and symmetric stretching vibrations of - the NH stretching vibration of the NH groups not bonded by a hydrogen bond.…”

Section: Canadian Journal Of Chemistry 49 3795 (1971)mentioning

confidence: 99%

“…In the case of the model substances, N H stretching vibrations of hydrogen-bonded N H groups in the 3400-3150 cm-' .range are observed (6,7). It could be assumed, accordingly, that both bands are caused by NH stretching vibrations of different bases.…”

Section: Canadian Journal Of Chemistry 49 3795 (1971)mentioning

confidence: 99%

Fermi Resonance of Infrared Vibrations in the —NH₂ Groups of Polynucleotides

Zuńdel¹,

Lubos²,

Kölkenbeck³

1971

Can. J. Chem.

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The —NH2 group causes an intensive band pair in the i.r. spectra of DNA, r.RNA, poly (A + U), and poly (G + C). One band occurs at 3330, another at 3180 cm−1. This band pair is due to the NH stretching vibration of the hydrogen-bonded NH group as well as to the harmonic vibration of the —NH2 bending vibration, whereby these vibrations are coupled via Fermi resonance. This follows on comparison with papers on amines. The weak shoulder in the 3500–3400 cm−1 range is to be assigned to the stretching vibrations of the non hydrogen-bonded NH groups. The doublet structure disappears to a large extent in the denaturated DNA, since the strength of the Fermi resonance depends on the strength of the hydrogen bonds and the hydrogen bonds are of differing strength, due to the bending and stretching. The relative intensities of the two bands are interchanged in the corresponding band pair of the —ND2 groups, for which an explanation can also be given.

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An Infrared Study of Hydrogen Bonding between Adenine and Uracil Derivatives in Chloroform Solution

Cited by 286 publications

References 1 publication

A Physical Chemist's Expedition to Explore the World of Membrane Proteins

A Physical Chemist's Expedition to Explore the World of Membrane Proteins

Preparation and Properties of Amphiphilic Polymer Nanospheres Containing Aza-crown ether

Fermi Resonance of Infrared Vibrations in the —NH₂ Groups of Polynucleotides

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An Infrared Study of Hydrogen Bonding between Adenine and Uracil Derivatives in Chloroform Solution

Cited by 286 publications

References 1 publication

A Physical Chemist's Expedition to Explore the World of Membrane Proteins

A Physical Chemist's Expedition to Explore the World of Membrane Proteins

Preparation and Properties of Amphiphilic Polymer Nanospheres Containing Aza-crown ether

Fermi Resonance of Infrared Vibrations in the —NH2 Groups of Polynucleotides

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Fermi Resonance of Infrared Vibrations in the —NH₂ Groups of Polynucleotides