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

Ruman, Tomasz; Długopolska, Karolina; Kuśnierz, Anna; Jurkiewicz, Agata; Leś, Andrzej; Rode, Wojciech

doi:10.1016/j.bioorg.2009.03.003

Cited by 9 publications

(1 citation statement)

References 28 publications

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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%

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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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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Structure, Properties, and Preparation of Boronic Acid Derivatives

2011

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Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds

et al. 2016

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Herein, we demonstrate the use of α‐boryl aldehydes and acyl boronates in the synthesis of aminoboronic acid derivatives. This work highlights the untapped potential of boron‐substituted iminium ions and offers insights into the behavior of N‐methyliminodiacetyl (MIDA) boronates during condensation and tautomerization processes. The preparative value of this contribution lies in the demonstration that various amines, including linear and cyclic peptides, can be readily conjugated with boron‐containing fragments. A mild deprotection of amino MIDA‐boronates enables access to α‐ and β‐aminoboronic acids in high chemical yields. This simple process should be applicable to the synthesis of a wide range of bioactive molecules as well as precursors for cross‐coupling reactions.

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

Cited by 9 publications

References 28 publications

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

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

Structure, Properties, and Preparation of Boronic Acid Derivatives

Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds

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