Biosynthesis structure elucidation

A useful volume on the chemistry of terpenoids and steroids has appeared.1 Nineteen topics in monoterpenoid chemistry are reviewed with a literature coverage to early 1973 the topics are particularly suitable for use in advanced lecture courses and cover biosynthesis, structural elucidation, and synthesis. Monoterpenoid alkaloid chemistry has been reviewed.2... 

After identification of A9-THC as the major active compound in Cannabis and its structural elucidation by Mechoulam and Gaoni in 1964 [66], a lot of work was invested in chemical synthesis of this substance. Analogous to the biosynthesis of cannabinoids, the central step in most of the A9-THC syntheses routes is the reaction of a terpene with a resorcin derivate (e.g., olivetol). Many different compounds were employed as terpenoid compounds, for example citral [67], verbenol [68], or chrysanthenol [69]. The employment of optically pure precursors is inevitable to get the desired (-)-trans-A9-THC. 

This chapter extends the information provided by the two preceding reviews (1,2) to the literature that appeared within the years 1976-1986, focusing on spectral data, structural elucidation, synthesis, biosynthesis, and pharmacology. Some references that appeared in the foregoing reviews are omitted from this chapter with exception of those related to the present treatise. Although previously presented in Volume 16 of this treatise (2), the numbering system of the hasubanan skeleton (la) and the hasubanalactam skeleton (lb), which is used in this chapter except for the most part of Section V, is represented anew. 

Metabolite biosynthesis has demonstrated its utility in drug metabolite preparation and characterization, and contributed to drag discovery and development. Although metabolite biosynthesis is a prerequisite step for metabolite structure elucidation in many cases, it is complementary to chemical synthesis in large-scale metabolite preparations. The merits for using these techniques should be determined on a case-by-case fashion. New techniques, such as recombinant enzyme and microbial glucuronidation systems, would have a great impact on the field. 

Zhang, D., Zhang, H., Aranibar, N. et al. (2006) Structural elucidation of human oxidative metabolites of muraglitazar use of microbial bioreactors in the biosynthesis of metabolite standards. Drug Metabolism and Disposition The Biological Fate of Chemicals, 34, 267-280. 

Bomati EK, Austin MB, Bowman ME, Dixon RA and Noel IP. 2005. Structural elucidation of chalcone reductase and implications for deoxychalcone biosynthesis. J Biol Chem 280 30496-30503. 

Abstract This chapter reviews chemical structures of biologically active, volatile compounds in beetles. Techniques used for structure elucidation are briefly discussed as well as facts and speculations on the biosynthesis of target compounds. Syntheses of selected substances are cursorily presented. The order of sections follows taxonomic classifications. Depending on the biological significance of relevant compounds in certain taxa, the corresponding sections are again subdivided into attractive compounds (mostly intraspecifically active pheromones) and defensive compounds (mostly interspecifically active allomones). 

Keywords Beetles Attractive compounds Pheromones Defensive compounds Biosynthesis Identification techniques Structure elucidation... 

ISOLATION, STRUCTURE ELUCIDATION, AND BIOSYNTHESIS OF THE BISINDOLE ALKALOIDS OF CATHARANTHUS... 

Dimise EJ, Widboom PF, Bruner SD (2008) Structure Elucidation and Biosynthesis of Fuscachelins, Peptide Siderophores from the Moderate Thermophile Thermobifida fusca. Proc Natl Acad Sci USA 105 15311... 

Holzenkampfer M, Walker M, Zeeck A, Schimana J, Fiedler H-P (2002) Simocyclinones, Novel Cytostatic Angucyclinone Antibiotics Produced by Streptomyces antibioticus Tii6040 II. Structure Elucidation and Biosynthesis. J Antibiot 55 301... 

MZ Kuo, RJ Zielinski, JI Cialdella, CK Marschke, MJ Dupui s, GP Li, DA Klooster-man, CH Spilman, VP Marshall. Discovery, isolation, structure elucidation and biosynthesis of U-106305, a cholesteryl ester transfer protein inhibitor from UC11136. J Am Chem Soc 117 10629-10634, 1995. 

Needham, J., Kelly, M. T., Ishige, M., and Andersen, R. J., Andrimid and moiramides A-C, metabolites produced in culture by a marine isolate of the bacterium Pseudomonas fluorescens structure elucidation and biosynthesis, J. Org. Chem., 59, 2058, 1994. 

Dewick PM (1989) Biosynthesis of lignans. In Atta-ur-Rahman (ed) Studies in natural product chemistry, vol 5 Structure elucidation (Part B). Elsevier, Amsterdam, p 459... 

David Morgan is a member of the Chemical Ecology Group at Keele University. He was bom in Newfoundland and had his university education there, at Dalhousie University and University of King s College in Halifax, Nova Scotia, and at Oxford. His doctorate thesis was on the lipids of Mycobacterium tuberculosis. He later worked at the National Institute for Medical Research in London, and for Shell Chemical Company and Shell Research under the direction of Sir Robert Robinson, O.M., Nobel Laureate. From 1966 he has been at Keele in Staffordshire as lecturer, senior lecturer, reader, and professor. He discovered the natural pesticide azadirachtin and collaborated with S. V. Ley for its final structure elucidation. He is the author of over 300 papers and reviews, mostly on insect chemistry, editor, and contributor to several volumes and author of the book Biosynthesis in Insects. ... 

An excellent review of the isolation, structural elucidation, total synthesis, and postulated biosynthesis of sesquiterpenoids based on the spiro[4,5]decane (vetis-pirane) skeleton has been published." Further studies on the development of alternative routes to the vetispirane sesquiterpenoids have been described. In one report100 the spirocyclic acetal (217), previously used as an intermediate in the synthesis of (—)-a-acorenol (218),101,102 has been converted into (—)-agarospirol (219) and (-)-/3-vetivone (220) by the reaction sequence outlined in Scheme 26. 

This chapter reviews the nitrogen-containing neurotoxic compounds produced by cyanobacteria, and follows an earlier review in this series which more broadly covered the alkaloid chemistry of these life forms from the marine environment [3]. A description of the discovery, isolation, structural elucidation, biosynthesis, mechanism of action, structure-activity relationship (SAR), and some aspects of chemical synthesis of cyanobacteria toxins is provided. 

The pentalane class of sesquiterpenoids has received substantial attention in the past year from the standpoints of structural elucidation, biosynthesis, and synthesis. Two new metabolites of this class are pentalenic acid (298) and pentalenolactone H (299). Both these compounds have a secondary hydroxyl function adjacent to the gem-dimethyl group and are thus potential precursors of pentalenolactone (300) in which one of these methyl groups has undergone a 1,2-migration. Cane and Rossi " have now identified a further metabolite of a Streptomyces strain which has been named pentalenolactone E (301) and is now... 

Many coenzymes (cofactors) involved in human and animal metabolism were discovered in the first half of the twentieth century, and their isolation and structure elucidation were hailed as milestones as shown by the impressive number of Nobel prizes awarded for research in that area. Studies on coenzyme biosynthesis were typically initiated in the second half of the twentieth century and have generated a massive body of literature that continues to grow rapidly because the area still involves many incompletely resolved problems. In parallel, numerous novel coenzymes were discovered relatively recently by studies of microorganisms. In this article, the terms cofactor and coenzyme are used as synonyms. 

---