Bioorganometallic chemistry. 8. The molecular recognition of aromatic and aliphatic amino acids and substituted aromatic and aliphatic carboxylic acid guests with supramolecular(η5-pentamethylcyclopentadienyl) rhodium-nucleobase,nucleoside,and nucleotide cyclic trimer hosts vianon-covalent π-πand hydrophobic interactions in water:Steric,electronic

Hong Chen, Seiji Ogo, Richard H. Fish

研究成果: Contribution to journalArticle査読

126 被引用数 (Scopus)

抄録

Molecular recognition, via non-covalent processes such as hydrogen bonding, π-π, and hydrophobic interactions, is an important biological phenomenon for guests, such as drugs, proteins, and other important biological molecules with, for example, host DNA/RNA. We have studied a novel molecular recognition process using guests that encompass aromatic and aliphatic amino acids [L-alanine, L-glutamine (L-Gln), L-histidine, L-isoleucine (L-Ile), L-leucine (L-Leu), L-phenylalanine (L-Phe), L-proline, L-tryptophan (L-Trp), L-valine (L-Val)], substituted aromatic carboxylic acids [o-, m-, p-aminobenzoic acids (G1-3), benzoic acid (G4), phenylacetic acid (G5), p-methoxyphenylacetic acid (G6), o-methyoxybenzoic acid (G9), o-nitrobenzoic acid (G10)], and aliphatic carboxylic acids [cyclohexylacetic acid (G7), 1-adamantanecarboxylic acid (G8)] with supramolecular, bioorganometallic hosts, (η5-pentamethylcyclopentadienyl)rhodium (Cp*Rh)-nucleobase, nucleoside, and nucleotide cyclic trimer complexes, [Cp*Rh(9-methyladenine)]3(OTf)3 (1) (OTf = trifluoromethanesulfonate), [Cp*Rh(adenosine)]3(OTf)3 (2), [Cp*Rh-(2′-deoxyadenosine)]3(OTf)3 (3), [Cp*Rh(2′,3′-dideoxyadenosine)]3(OTf)3 (4), and [Cp*Rh(Me-5′-AMP)]3 (5), in aqueous solution at pH 7, utilizing 1H NMR, NOE, and molecular modeling techniques, and, as well, determining association constants (Ka) and free energies of complexion (ΔG°). The host-guest complexation occurs predominantly via non-covalent π-π, hydrophobic, and possible subtle H-bonding interactions, with steric, electronic, and molecular conformational parameters as important criteria. Moreover, we note that both the π-π and hydrophobic interactions seem to be equally important when competing aromatic and aliphatic carboxylic acid guests, G5 and G7, for host 3. The solvophobic effects in H2O also control the extent of host-guest interaction and will be discussed.

本文言語英語
ページ(範囲)4993-5001
ページ数9
ジャーナルJournal of the American Chemical Society
118
21
DOI
出版ステータス出版済み - 5 29 1996
外部発表はい

All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

フィンガープリント

「Bioorganometallic chemistry. 8. The molecular recognition of aromatic and aliphatic amino acids and substituted aromatic and aliphatic carboxylic acid guests with supramolecular(η<sup>5</sup>-pentamethylcyclopentadienyl) rhodium-nucleobase,nucleoside,and nucleotide cyclic trimer hosts vianon-covalent π-πand hydrophobic interactions in water:Steric,electronic」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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