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

Research output: Contribution to journalArticle

124 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4993-5001
Number of pages9
JournalJournal of the American Chemical Society
Volume118
Issue number21
Publication statusPublished - May 29 1996
Externally publishedYes

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Molecular recognition
Aromatic Amino Acids
Rhodium
Cyclic Nucleotides
Carboxylic Acids
Hydrophobic and Hydrophilic Interactions
Carboxylic acids
Nucleosides
Amino acids
Fatty Acids
Amino Acids
Acids
Water
Dideoxyadenosine
Nitrobenzoates
4-Aminobenzoic Acid
Biological Phenomena
Benzoic Acid
Molecular modeling
Isoleucine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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title = "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",
abstract = "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.",
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T1 - 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

AU - Chen, Hong

AU - Ogo, Seiji

AU - Fish, Richard H.

PY - 1996/5/29

Y1 - 1996/5/29

N2 - 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.

AB - 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.

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