tg, gg, and gt conformers, illustration, 165f

Subject Index

Downloaded by 80.82.77.83 on April 21, 2018 | https://pubs.acs.org Publication Date (Web): November 2, 2017 | doi: 10.1021/bk-2017-1257.ix002

A

tg, gg, and gt conformers, illustration, 165f

ACS, update on international activities ACS global alliances, 96 ACS International Activities’ interactions with Cuba, 101 ACS international center, 99 ACS-Pittcon collaboration, 100 ACS science and human rights, 98 Global Innovation Imperatives (Gii), 100 International Chemical Sciences Chapters, 97 introduction, 95 lessons learned, 101 U.S. Department of State workshops on ethics, 100

C Cyano group, anomeric effect experimental computational methods, 166 crystallography, 166 2,3-Dideoxy-α-D-erythrohexopyranosyl cyanide 4, 167 2,3-Dideoxy-α-D-erythrohexopyranosyl cyanide 7, 168 general procedures, 166 introduction, 155 generalized anomeric effect, 156f results and discussion, 157 B3LYP/6-31+G, 162t B3LYP/6-311++G, 163t B3LYP/6-311++G gas-phase calculated geometrical parameters, 164t B3LYP/6-311++G gas-phase calculated relative enthalpy, 165t 2,3-dideoxy-α-D-erythrohexopyranosyl cyanide, 158s 2,3-dideoxy-α-D-erythrohexopyranosyl cyanide, synthesis, 158s glycosyl cyanides, selected bond distances, 160f ORTEP diagrams, 159f Serianni et al, model compounds studied, 165f structures analyzed, 161f

E Educational outreach activities conclusion, 61 future ACS-SCQ interactions, 61 initial efforts, 59 introduction, 57 2016 Simposio Internacional de Química, 59 Ernest Eliel session, program, 60t Eliel, Ernest L. Eliel, Ernest, the man celebrating a high enantiomeric excess, 31f compounds synthesized by the Eliel group, examples, 30s Ernest and Eva after a luncheon, 32f global chemical community, citizen, 29 Eliel, Ernest, the scientist neoisomenthol, 19s obtaining non-racemic compounds, Eliel’s scheme, 17s stereochemistry, early interest, 16 Tamelen’s yohimbine papers, 18 Eliel’s happiest moments in life, in science, 33 after receipt of the D.Sc. degree at Duke University, 34f Chemical & Engineering News, cover, 35f Ernest as my hidden advisor, 36 Benfey, Ted, 40f Eliel holding manuscript, 38f hidden advisory role, 39 Virginia plantation, Ernest and the author, 37f hidden advisors, Ernest’s interest, 35 Woodward, R. B., in his January 9, 1970 letter, 36f introduction, 13 August 22, 2016 symposium, participants, 15f Eliel’s autobiography, cover, 16f several individuals, earlier photograph, 15f our last time together, 41

219 Cheng et al.; Stereochemistry and Global Connectivity: The Legacy of Ernest L. Eliel Volume 1 ACS Symposium Series; American Chemical Society: Washington, DC, 2017.


parting, 42 Read, John, 20 chemistry building, Notre Dame, 27f Eliel’s chiral template, preparation, 28s enantiomers of mevalolactone, synthesis, 29s from stereochemistry to synthesis, 22 stereoselective reactions, 28s stereospecific reactivity, first observation, 28s various saturated heterocycles, summary, 26s Ernest Eliel Workshop: US and Cuba Collaboration in Chemistry Education and Neglected Disease Drug Discovery, 63 assessment Cuban student perspectives and reflections, 83 dissemination of knowledge and equipment, chemical education, 82 goals, 81 non-existent unemployment rate, Cuba, 86 Sanchez, Juan (IUPUI), 87 scientific exchange, 81 student poster presentation, 82f Tiano, Daniel (Santa Clara University), 88 USA student TAs relaxing, 85f US student perspectives and reflections, 85 final thoughts, 90 future collaborations, plans distributed drug discovery dissemination, 90 research collaborations, 89 introduction Cuban Workshop, foundation, 64 workshop, lab component, 76 carrying out the D3 procedure, 80f carrying out the lab work, 79 lab students and TAs, 77f replicated teams, bill-board layout, 78f sample of A1 purified by students, 1H spectra, 81f 22 structurally unique compounds, 79f undergraduate TAs, training, 77 workshop, lecture component, 66 bill-board equipment, 70f D3 virtual catalogs, lecture on compound enumeration, 75 lecture presentation, 68f lectures at a macro level, 67

lunch between lectures and lab, 67f more detailed and applied work, lectures, 71 N-acylated natural α-amino acids, synthesis, 74s new D3 lab 9, 73s new molecules to make, student team, 72f nine D3 protocols, 69s representative molecules, 71f workshop overview Cuba Workshop participants, 66f daily program, 66 participants, 65

S Saccharide stereochemistry, hydration-mediated effects conclusions, 190 experimental section differential scanning calorimetry (DSC), 175 fourier transform infra red (FTIR) spectroscopy, 175 materials, 174 methods, 174 introduction, 171 isomeric monosaccharides, 173f results and discussion, 176 aldohexose hydration number, Kd as a function, 182f β-lg, second-derivative spectra, 189f β-lg native conformation content, 188f β-lg with isomeric monosaccharides, interaction curves, 178f β-lg with isomeric monosaccharides, titration curves, 179f calibration protein samples, infra red spectra, 187f ΔTd vs. monosaccharide concentration, 181f disaccharide cellobiose, ΔTd as a function of concentration, 184f disaccharide hydration number, Kd as a function, 185f DSC study, 180 equatorial OH groups, Kd values vs. the average number, 183f FTIR study, 185 native and denatured β-lg, infra red spectra, 186f sugar and urea titrations, raw ITC plots, 177f



sugar hydration number, Kdf as a function, 189f Service of humanity, science and knowledge, 49 Prof. Eliel, 52f Stable isotopes, saccharide structure and reactivity, 105 concluding remarks, 150 introduction, 106 molecular structure, hierarchies, 106s saccharide anomerization, 107 aldehyde and hydrate forms in aqueous solutions, percentages, 112f anomerization equilibria and kinetics, 121s aqueous solution, percentages, 118t C1 chemical shifts, 110t C1 in the cyclic and acyclic forms, 13C chemical shiftsa, 111t 13C Saturation transfer experiment, 120f C1 signal of the hydrate form, appearance, 111f cyclic and acyclic forms, percentages, 117f cyclic and acyclic forms of D-[1-13C]threose in aqueous solution, percentages, 115f D-[1-13C]aldohexoses, percentages, 119t D-[1-13C]mannose, 13C{1H} NMR spectrum, 109f D-[2-13C]xylulose, anomerization, 116s D-erythrose, anomerization, 118s exchange between cyclic and acyclic forms, general scheme, 108s Neu5Ac, anomerization, 114s partial 13C{1H} NMR spectrum, 113f pH dependencies, 121f saccharides, stereospecific carbon skeletal rearrangements, 142 bimolybdate complexes, interconversion, 143s C1 and/or C2 of aldoses, introduction, 144s C1-C2 transposition, potential (untested) mechanism, 149s 13C-labeled products, 146s cyanohydrin reduction, synthetic routes, 144s D-[2-13C]glucosone, degradation, 147s degradation of D-[1,3-13C2]glucosone, reaction partitioning observed, 149s

2,3-dicarbonyl sugar, hypothetical reaction, 146s phosphate complexes, proposed formation, 149s reaction mixture, 13C{1H} NMR spectrum, 148f two reactions, 145s saccharide structure and anomerization kinetics, relationships, 122 N-formyl and N-acetyl side-chains, 133 aldofuranose ring, proposed anchimeric mechanism, 123s anomerization, unidirectional rate constants, 125t anomerization equilibria in furanose ring systems, Thorpe-Ingold effects, 127t anomerization rate constants, Thorpe-Ingold effects, 128t O-acetyl side-chains, 139 carbonyl carbon signal intensity, plots, 138f carbonyl signals, 13C{1H} NMR spectrum, 136f carboxyl group, 130 13C-labeled mono-O-acetylated D-glucopyranoses, 141s C3–O3 fragment, Newman projection, 142s common side-chains, structures, 132s C4-substituted aldofuranose rings, structures, 122s CTI rate constants, 139f equilibrium constants, 135f experimental J-couplings, 139 furanose ring deoxygenation, effects, 126 1H NMR spectrum, 134f intramolecular catalysis, possible modes, 131s intramolecular catalysis, proposed mechanism, 129s 3JH2,NH, dependencies on, 137f ketopentoses, 124 kopen, plots, 127f Newman projection, 136s N-formyl and N-acetyl side-chains, structural properties, 132s O-acetyl side-chains, aminosugars and conformational properties, 131 penturonic acids, ring-opening rate constants, 131t preferred ring conformations, 128s probability distributions, 141f ring-opening rate constants, 129t


P(GM-NMG), synthesis, 199 polymer-enhanced ultrafiltration, 200 ultrafiltration membranes, purification, 199 washing method, 201 introduction, 198 results and discussion As, Cr, and B as a function of pH, removal profiles, 205f As, Cr, and B in the presence of interfering ions, removal profiles, 208f maximum retention capacity, 208t P(GM-NMG), boron retention capacity, 204 P(GM-NMG), characterization, 202 P(GM-NMG), molecular weight, 203t polymer concentration, influence, 206 polymer-enhanced ultrafiltration, removal of oxyanions, 203 polymer:metal molar ratio, removal profiles, 207f potentiometric titration, 202f

several aldotetroses and C5-modified aldopentoses, ring-opening rate constants, 123t Stereochemistry and global connectivity carbohydrates, 5 conclusions, 6 global connectivity, 3 introduction, 1 NMR applications, 5 organic compounds, stereochemistry, 4 tribute to Eliel, 3


W Water, removal of pollutant oxy-anions, 197 conclusions, 209 experimental section enrichment method, 201 monomer GM-NMG and polymer P(GM-NMG), preparation, 200f P(GM-NMG), characterization, 200


tg, gg, and gt conformers, illustration, 165f

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