Synthesis and NMR properties of derivatives of 5,6-dihydroborauracil and 5,6-dihydroborathymine

Ruman, Tomasz; Długopolska, Karolina; Kuśnierz, Anna; Rode, Wojciech

doi:10.1016/j.bioorg.2009.07.004

Cited by 7 publications

(7 citation statements)

References 17 publications

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“…55). [180][181][182][183][184][185] The synthesis of borauracils (123-130) starts with the reaction of nitrile 131 with a strong base providing the substituent at the C6 position of the final product. The formal imino group formed is then protected with trimethylchlorosilane and further reacted with trimethylsilyltriflate to give the N,N-bis(trimethylsilyl)enamine (132).…”

Section: -Dihydroxyboryldeoxyuridine (85) Was Tested In Vitro Onmentioning

confidence: 99%

“…This was a challenging issue as the standard 5 0 -dimethoxytrityl group usually used in standard phosphoramidite chemistry is incompatible with the preparation of borane phosphonate DNA. Using appropriately protected 5 0 -O-[benzhydroxybis(trimethylsilyloxy)]silyl phosphoramidites (179)(180)(181)(182), they carried out a high yielding synthesis cycle compatible with the synthesis of boranophosphate DNA (183) (Fig. 72).…”

Section: Change On the Phosphatementioning

confidence: 99%

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Boron and nucleic acid chemistries: merging the best of both worlds

2013

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At the intersection of nucleic acid and boron chemistries lies a thriving world of possibilities. During the past decades, the merging of these research domains has led to fascinating discoveries in different fields ranging from material to medical sciences. In recent years the interplay of these two worlds has gained a lot of attention, as can be judged by the increasing number of articles in which boron and nucleic acids stand out for their potential medicinal, biotechnological or analytical applications. In this review, we present an outline of this crossroads by focusing on both the interaction of boronated compounds with nucleic acids and the modification of nucleic acids by boron containing moieties.

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Section: -Dihydroxyboryldeoxyuridine (85) Was Tested In Vitro Onmentioning

confidence: 99%

Section: Change On the Phosphatementioning

confidence: 99%

Boron and nucleic acid chemistries: merging the best of both worlds

2013

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“…Several types of boronated nucleobases with a carborane group inserted to the pyrimidine moiety at the N3‐position or C5‐position. There are few known boron analogues of nucleic acid bases, including benzo‐borauracils, 5,6‐dihydroborauracils, 5,6‐dihydroborathymines, and boracytosines . The first derivatives of boron analogous of uracil, containing boron at 4‐position of heterocyclic ring, were presented by Soloway and colleagues in 1990 .…”

Section: Introductionmentioning

confidence: 99%

“…There are many interesting questions on boron analogous of uracil nucleobase concerning, for example their relative stability order, electronic structure, chemical properties and base‐pairing ability to adenine nucleobase. In an attempt to answer these questions, density functional theory (DFT) and second‐order Møller–Plesset (MP2) computational methods in conjunction with 6‐311++ G (d,p) atomic basis set were chosen to study two boron analogues of uracil, which were recently synthesized by Ruman et al . (Scheme ) in gas phase and aqueous solution by adopting integral equation formalism of the polarized continuum model (IEF‐PCM).…”

Section: Introductionmentioning

confidence: 99%

What roles do boron substitutions play in structural, tautomeric, base pairing and electronic properties of uracil? NBO & AIM analysis

Tehrani

Abedin

Shakourian‐Fard

et al. 2012

J of Physical Organic Chem

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The synthesis of modified versions of deoxyribonucleic acid is an area that is receiving much attention. The replacement of the nitrogen atom on the nucleobases with boron atom has provided insight into deoxyribonucleic acid and ribonucleic acid stability, recognition, and replication at the atomic level. In the present research, we investigated a detailed density functional theory study of the structural, tautomeric, base-pairing ability, bond dissociation energy, and electronic properties of two boron analogues (i.e., boron substitutions at 4-position and 5-position of uracil) of uracil nucleobase. The effects of these modifications on theirs acid-base properties have been considered. Our goal is to gather data to help elucidate the structure and electronic properties of boron analogues of uracil. Density functional theory calculations were performed using a nonlocal hybrid B3LYP and 6-311++G (d,p) atomic basis set. The result of calculation revealed that the canonical 'keto' form is the most stable tautomeric form of uracil nucleobase and its boronated analogues in the gas phase at density functional theory and second-order Møller-Plesset levels. Hyperconjugation stabilization factors that affect the stability of generated radicals and anions in these molecules were investigated by natural bond orbital analysis. Furthermore, quantum theory of atoms in molecules analysis was performed to extract the bond critical point properties of various base pairs. The electron density can be considered as a good description of the strength of the different types of hydrogen bonding.

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“…The rigidity of the cyclic boronate derivatives of corresponding 1,2- or 1,3-diols, requiring relatively fixed conformations, is used in nuclear magnetic resonance (NMR) studies of carbohydrate concentrations and the position of their functional groups [ 26 ]. The B 11 -NMR resonance of boron esters is a broad line and its spectra allow distinction between five, six, seven-member cyclic and acyclic boronates [ 27 , 28 , 29 ]. Suitable boronate single crystals are useful for X-ray diffraction to establish the conformation and the absolute configuration of the molecule in the crystalline state [ 22 , 30 , 31 ].…”

Section: Introductionmentioning

confidence: 99%