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Articles 1 - 6 of 6
Full-Text Articles in Chemistry
Characterization And Reaction Of An Analog Of The Anticancer Drug Oxaliplatin, Jonathan D. Hendrie
Characterization And Reaction Of An Analog Of The Anticancer Drug Oxaliplatin, Jonathan D. Hendrie
Mahurin Honors College Capstone Experience/Thesis Projects
Oxaliplatin is an anticancer drug that reacts with DNA, RNA, and proteins both in vitro and in vivo. Our research focuses on synthesizing analogs of oxaliplatin and understanding how bulky ligand groups affect reaction with amino acids. (R,R)-N,N’-dimethyl-1,2-diaminocyclohexane platinum(II) oxalate or Pt(Me2dach)(ox) varies from oxaliplatin or Pt(dach)(ox) in that it has one methyl group attached to each platinum coordinated nitrogen. Nuclear Magnetic Resonance (NMR) spectroscopy has shown that the reactions of N-Acetylmethionine (N-AcMet) with Pt(Me2dach)(ox) and Pt(dach)(ox) proceed at similar rates suggesting that the methyl groups of Pt(Me2dach)(ox) have little effect on the initial reaction. Whereas the reaction of Pt(dach)(ox) …
Interplay Of Hydrogen Bonds And N→Π* Interactions In Proteins, Gail J. Bartlett, Robert W. Newberry, Brett Vanveller, Ronald T. Raines, Derek N. Woolfson
Interplay Of Hydrogen Bonds And N→Π* Interactions In Proteins, Gail J. Bartlett, Robert W. Newberry, Brett Vanveller, Ronald T. Raines, Derek N. Woolfson
Brett VanVeller
Protein structures are stabilized by multiple weak interactions, including the hydrophobic effect, hydrogen bonds, electrostatic effects, and van der Waals interactions. Among these interactions, the hydrogen bond is distinct in having its origins in electron delocalization. Recently, another type of electron delocalization, the n→π* interaction between carbonyl groups, has been shown to play a role in stabilizing protein structure. Here we examine the interplay between hydrogen bonding and n→π* interactions. To address this issue, we used data available from high-resolution protein crystal structures to interrogate asparagine side-chain oxygen atoms that are both acceptors of a hydrogen bond and donors of …
Sequence-Specific Inhibition Of A Nonspecific Protease, Leigh A. Logsdon, Adam R. Urbach
Sequence-Specific Inhibition Of A Nonspecific Protease, Leigh A. Logsdon, Adam R. Urbach
Chemistry Faculty Research
A nonspecific exopeptidase, aminopeptidase N (APN), is inhibited sequence-specifically by a synthetic host, cucurbit[7]uril (Q7), which binds with high affinity and specificity to N-terminal phenylalanine (Phe) and 4-(aminomethyl)phenylalanine (AMPhe) and prevents their removal from the peptide. Liquid chromatography experiments demonstrated that in the presence of excess Q7, APN quantitatively converts the pentapeptides Thr-Gly-Ala-X-Met into the dipeptides X-Met (X = Phe, AMPhe). The resulting Q7-bound products are completely stable to proteolytic digestion for at least 24 h. Structure–activity studies revealed a direct correlation between the extent of protection of an N-terminal amino acid and its affinity for Q7. Therefore, Q7 provides …
(S)-Trifluoroselenomethionine : A New Non-Natural Amino Acid With Enhanced Methioninase-Induced Cytotoxicity Toward Human Colon Cancer Cells, Stephene Nathele Lodge
(S)-Trifluoroselenomethionine : A New Non-Natural Amino Acid With Enhanced Methioninase-Induced Cytotoxicity Toward Human Colon Cancer Cells, Stephene Nathele Lodge
Legacy Theses & Dissertations (2009 - 2024)
Abstract
Asymmetric Synthesis Of \Alpha-(Heteroaryl)Alkylamines And \Alpha -Amino Acids Via Nucleophilic 1,2-Addition Of Lithiated Heterocycles To Aldehyde Samp-Hydrazones, Dieter Enders, Giuseppe Del Signore, Gerhard Raabe
Asymmetric Synthesis Of \Alpha-(Heteroaryl)Alkylamines And \Alpha -Amino Acids Via Nucleophilic 1,2-Addition Of Lithiated Heterocycles To Aldehyde Samp-Hydrazones, Dieter Enders, Giuseppe Del Signore, Gerhard Raabe
Turkish Journal of Chemistry
The asymmetric synthesis of \alpha-(heteroaryl)alkylamines was accomplished by employing a diastereoselective nucleophilic 1,2-addition of lithiated aromatic heterocycles to aldehyde SAMP-hydrazones, followed by BH_3 . THF or SmI_2 promoted removal of the chiral auxiliary. The CBz or benzoyl-protected amines were obtained in good yields (40\%--78\%) and excellent enantiomeric excesses (ee = 88\%--99\%). The methodology can be applied to the synthesis of highly enantioenriched \alpha-amino acids (ee = 90\%--99\%).
C_2-Symmetric Chiral Diamine Ligands For Enantiomeric Recognition Of Amino Acid Esters And Mandelic Acid By Proton Nmr Titration Method, Hayri̇ye Aral, Tarik Aral, Mehmet Çolak, Berri̇n Zi̇yadanoğullari, Recep Zi̇yadanoğullari
C_2-Symmetric Chiral Diamine Ligands For Enantiomeric Recognition Of Amino Acid Esters And Mandelic Acid By Proton Nmr Titration Method, Hayri̇ye Aral, Tarik Aral, Mehmet Çolak, Berri̇n Zi̇yadanoğullari, Recep Zi̇yadanoğullari
Turkish Journal of Chemistry
Two novel C_2-symmetric chiral diamines containing \alpha -phenylethyl and \alpha -(1-naphthyl)ethyl chiral subunits were prepared with quantitative yields. Enantiomeric recognition properties of these simple structured diamine ligands towards D- and L-amino acid esters and D- and L-mandelic acid were examined by the ^1H NMR titration method. These ligands exhibited strong complexation (with K_f up to 2481 M^{-1}) and good enantioselectivity (up to K_L/K_D = 4.08) towards the mandelic acid enantiomers. The results show that simple structured and easily accessible acyclic C_2-symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex …