14.4. What Are the Structures, Names, and Properties of Thiols?, 411
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Nature's Way To Make the LantibioticsHeather A. Relyea and Wilfred A. van der Donk This article focuses on one class of antimicrobial compounds, the lantibiotics, and discusses their biosynthetic pathways as well as their molecular mode of action. In the course of the review, the meaning of the terms regio-, chemo-, and stereoselectivity are discussed. Relyea, Heather A.; van der Donk, Wilfred A. J. Chem. Educ.2006, 83, 1769.
Applications of Chemistry |
Bioorganic Chemistry |
Biotechnology |
Biosynthesis |
Catalysis |
Drugs / Pharmaceuticals |
Proteins / Peptides
The Discovery and Development of CisplatinRebecca A. Alderden, Matthew D. Hall, and Trevor W. Hambley Cisplatin is currently one of the most widely used anticancer drugs in the world. The unlikely events surrounding the discovery of its anticancer activity, subsequent introduction into the clinic, and the continuing research into platinum compounds is the subject of this review. Alderden, Rebecca A.; Hall, Matthew D.; Hambley, Trevor W. J. Chem. Educ.2006, 83, 728.
Bioinorganic Chemistry |
Coordination Compounds |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Metallic Bonding |
Oxidation State |
Synthesis
Volatile Organic Sulfur Compounds of Environmental Interest: Dimethyl Sulfide and Methanethiol. An Introductory OverviewThomas G. Chasteen and Ronald Bentley Volatile organic sulfur compounds and their degradation products play important environmental roles in global warming, acid precipitation, and cloud formation. Two important members of this group, dimethyl sulfide, DMS, and methanethiol, MT, are formed by living organisms as well as by abiotic processes. The chemical reactions responsible for the biosynthesis of DMS and MT are emphasized here, as well as means for their degradation. Since sulfur compounds are often ignored in normal course work, this article provides a basic foundation for an understanding of these interesting and environmentally significant compounds. Chasteen, Thomas G.; Bentley, Ronald. J. Chem. Educ.2004, 81, 1524.
Molecular Models of Plant HormonesWilliam F. Coleman The paper "Synthesis of Plant Auxin Derivatives and Their Effects on Ceratopteris richardii" by Corey E. Stilts and Roxanne Fisher describing an experiment begun in the organic labs and completed in a biochemistry cell biology lab provides the featured molecules for this month. The molecules in Figure 1 of that paper have been added to the collection. There is nothing particularly surprising about their structures, but students might be interested in seeing whether they can determine any structure/regulating effect relationships as the number of synthesized auxin derivatives grows. Additionally, students with little or no biochemistry background might wish to explore other systems that act as growth regulating hormones in plants, as an introduction to the variety of molecular structures that can display such bioactivity. Such molecules range from the very simple, ethene, to the adenine-derived cytokinins (an example of which, zealtin, is shown here) and the brassinosteroids. Brassinolide, a commonly occurring brassin, is also shown. These latter two structures have also been added to the molecule collection. All of the structures have been optimized at the HF/6-31G(d) level.
Synthesis |
Biological Cells |
Hormones |
Bioorganic Chemistry
The Chemistry of CoffeeWilliam F. Coleman The paper Our Everyday Cup of Coffee: The Chemistry behind Its Magic by Marino Petracco provides a hearty blend of molecules for this month. The author deals with coffee at a number of different levels ranging from the economic and social to the still perplexing questions of flavor and aroma. The associated molecules demonstrate a range of structural features that students will benefit from examining in three dimensions.
Bioorganic Chemistry
Molecular Model of TubocurarineWilliam F. Coleman Curare, the Karib name for the plant from which this molecule is derived, is used in traditional South American medicine and hunting because it is a muscle relaxant. The three papers by Brunsvold and Ostercamp (1, 2, 3) provide us with an abundance of candidates for Featured Molecules this month. All of the major compounds highlighted in the papers, and many of the intermediates in the synthetic schemes, have been added to our collection. Students should note the structural similarities of the various barbiturate species and of the steroid-based compounds, as well as the interesting proto-cage structure of curare. Careful examination of the conformation of the alkyl groups in various of the molecules, when looked at as Newman projections, should convince students that their expectations about staggering substituents on adjacent tetrahedral-like carbon atoms are met in the computations. However, they should also be aware that recent work casts some doubt on the traditional explanation for that staggering (1). Charged species are presented in the collection in ionic form, without counterions (those are given in the papers), and all species except curare and atricurium besylate (molecule 40 in the third paper) were optimized at either HF/631-G(d) or B3LYP/631-G(d). The latter two molecules were optimized using HF/STO-3.
