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Organic Chemistry Commons

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2012

Selected Works

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Articles 1 - 9 of 9

Full-Text Articles in Organic Chemistry

A Discovery-Oriented Approach To Solid-Phase Peptide Synthesis, Brian B. Brennan, Matthew R. Bockman, Christopher J. Miedema Oct 2012

A Discovery-Oriented Approach To Solid-Phase Peptide Synthesis, Brian B. Brennan, Matthew R. Bockman, Christopher J. Miedema

Brian B. Brennan

In this discovery-oriented laboratory experiment, students use solid-phase synthesis techniques to construct a dipeptide containing an unknown amino acid. Following synthesis and cleavage from the polymeric support, electrospray ionization-mass spectrometry is employed to identify the unknown amino acid that was used in the peptide coupling. This experiment, performed in two, 3-h laboratory periods, provides an opportunity for students to learn the technique of solid-phase peptide synthesis and to critically evaluate data that they generate in the laboratory. The experiment is suitable for second-semester organic chemistry students as they learn methods for the formation of amide bonds or upper-level biochemistry students ...


2-Allylphenyl Glycosides As Complementary Building Blocks For Oligosaccharide And Glycoconjugate Synthesis, Hemali D. Premathilake, Alexei V. Demchenko Apr 2012

2-Allylphenyl Glycosides As Complementary Building Blocks For Oligosaccharide And Glycoconjugate Synthesis, Hemali D. Premathilake, Alexei V. Demchenko

Alexei Demchenko

The O-allylphenyl (AP) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of efficient oligosaccharide assembly.


Organic Chemistry: A Survival Guide For Students, Ethan C. Levine Apr 2012

Organic Chemistry: A Survival Guide For Students, Ethan C. Levine

Anton Geiler

This project reviews material from undergraduate Organic Chemistry I and II. It is meant to function as a supplement to the textbook and lecture material for the course as it is taught in universities throughout the United States. Complex ideas are broken down into simpler ones. Material is presented in conversational language, using as little scientific jargon as possible.


The Synthesis And Biological Evaluation Of Tamandarin B Analogs, Kenneth Lassen Feb 2012

The Synthesis And Biological Evaluation Of Tamandarin B Analogs, Kenneth Lassen

Kenneth Lassen

The tamandarin and didemnins are a class of cyclodepsipeptides that have shown a wide range of biological activity. The didemnins have demonstrated antitumor, antiviral and immunosuppressive activity at low nano- and femtomolar levels. Didemnin B was the first marine natural product to enter clinical trials in humans in the United States. The structures of tamandarins A and B were reported in 2000 and possess almost identical structure and biological activity to didemnin B. These compounds have shown impressive biological activity and some progress has been made in establishing structure-activity relationships. However, their molecular mechanism of action is still unclear. The ...


Environmentally Friendly Organic Synthesis Using Bismuth(Iii) Compounds, Ram Mohan, Scott Krabbe Dec 2011

Environmentally Friendly Organic Synthesis Using Bismuth(Iii) Compounds, Ram Mohan, Scott Krabbe

Ram S. Mohan

Abstract With increasing environmental concerns, the need for environmentally friendly organic synthesis has gained increased importance. In this regard, bismuth (III) compounds are especially attractive as “green” reagents and catalysts for organic synthesis. Bismuth(III) compounds are remarkably nontoxic, relatively air and moisture stable, and easy to handle. The contributions from our laboratory in the last 5 years in the field of applications of bismuth(III) compounds as catalysts are presented.


Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram S. Mohan, Neil J. Baldwin, Anna N. Nord, Brendan D. O’Donnell Dec 2011

Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram S. Mohan, Neil J. Baldwin, Anna N. Nord, Brendan D. O’Donnell

Ram S. Mohan

Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.


Selective Recognition Of H2po4 By A Cholestane-Imidazole-Zinc Ensemble, Jyoti Ramesh Jadhav, Md Wasi Ahmad, Hong Seok Kim Dec 2011

Selective Recognition Of H2po4 By A Cholestane-Imidazole-Zinc Ensemble, Jyoti Ramesh Jadhav, Md Wasi Ahmad, Hong Seok Kim

Dr. Mohammad Wasi Ahmad (Md Wasi Ahmad)

A new facile amphiphile cholestane-based zinc complex 4 containing a 3-aminopropylimidazole moiety at the 3a and 7a positions of cholestane was designed and synthesized. Recognition selectivity of the new receptor 4 with various anions was assessed by 1H NMR titration. Dihydrogen phosphate showed the highest binding affinity among all the tested anions


Fluorescein-Polyethyleneimine Coated Gadolinium Oxide Nanoparticles As T1 Magnetic Resonance Imaging (Mri)–Cell Labeling (Cl) Dual Agents, Wenlong Xu, Ja Young Park, Krishna Kattel, Md Wasi Ahmad, Badrul Alam Bony, Woo Choul Heo, Seonguk Jin, Jang Woo Park, Yongmin Chang, Tae Jeong Kim, Ji Ae Park, Ji Yeon Do, Kwon Seok Chae, Gang Ho Lee Dec 2011

Fluorescein-Polyethyleneimine Coated Gadolinium Oxide Nanoparticles As T1 Magnetic Resonance Imaging (Mri)–Cell Labeling (Cl) Dual Agents, Wenlong Xu, Ja Young Park, Krishna Kattel, Md Wasi Ahmad, Badrul Alam Bony, Woo Choul Heo, Seonguk Jin, Jang Woo Park, Yongmin Chang, Tae Jeong Kim, Ji Ae Park, Ji Yeon Do, Kwon Seok Chae, Gang Ho Lee

Dr. Mohammad Wasi Ahmad (Md Wasi Ahmad)

We report the synthesis, characterization and application of highly water-soluble fluoresceinpolyethyleneimine (PEI) coated gadolinium oxide (Gd2O3) nanoparticles to magnetic resonance imaging (MRI) and cell labeling (CL). The average particle diameter and average hydrodynamic diameter were estimated to be 3.92 and 7.5 nm, respectively. Fluorescein-PEI was prepared from EDC/NHS coupling method. The surface coating was characterized by the FT-IR absorption spectrum and the surface coating amount was estimated to be 22.42 wt% from a TGA analysis, corresponding to 0.65 nm22 grafting density. The fluorescein-PEI coated gadolinium oxide nanoparticles showed r1 and r2 of 6.76 and ...


Parallel Text Immersion, Daniel P. Becker Ph.D. Dec 2011

Parallel Text Immersion, Daniel P. Becker Ph.D.

Daniel P. Becker

A new method of teaching foreign languages to beginning, intermediate, and advancing foreign language students is proposed involving reading out loud passages, chapters, and entire works of literature that are familiar to the student through required pre-reading in the students’ mother tongue. Testing is proposed to evaluate the success of the method.