Ylindrospermopsin Alkaloids Research Paper Example | Topics and Well Written Essays - 2500 words

Ylindrospermopsin Alkaloids - Research Paper Example CHAPTER 1: INTRODUCTION The description of cylindrospermopsin alkaloids is such that they consist of three soluble water toxins that comprise of cylindrospermopsin (CYN) (1), 7-deoxy-cylindrospermopsin (7-deoxy-CYN) (2) and also 7-epi-cylindrospermopsin (7-epi-CYN) (3). Researchers have signaled towards certain problems related to the toxicological characteristics of these natural compounds, their existence in water and which was followed by their removal. The structural features of these alkaloids are in fact extraordinary comprising of a sulfonated tricyclic guanidine linked to a uracil ring. The beginning of this analysis centers on the isolation of these innate products followed by the investigation into the environmental impact of cylindrospermopsin alkaloids contamination. (1) Figure 1. The cylindrospermopsin alkaloids of cylindrospermopsin (1),7-deoxy-cylindrospermopsin (2) and 7-epi-cylindrospermopsin (3). 1.1 ISOLATION AND CHARACTERIZATION Credited to Moore and his team usin g a combination of NMR and mass spetroscopy, the extraction of Cylindrospermopsin (1) took place in 1992 from the cyanobacterium Cylindrospermopsis raciborskii. While 7-deoxy-cylindrospermopsin (2) was discovered in 1999, owing to the purification of cylindrospermopsin which was performed on a regular basis. It was also concluded that the derivate of cylindrospermopsin could also exist in the form of a pair of tautomers because of the fact that the uracil ring’s vinylic proton was not identified during the application of the H NMR technique as shown in figure 2. However, as every sample of 7-deoxy-cylindrospermopsin (2) was observed the incidence of the uracil group (4) was confirmed by examining the absorbance maximum (?max). Even... Credited to Moore and his team using a combination of NMR and mass spetroscopy, the extraction of Cylindrospermopsin (1) took place in 1992 from the cyanobacterium Cylindrospermopsis raciborskii. While 7-deoxy-cylindrospermopsin (2) was discovered in 1999, owing to the purification of cylindrospermopsin which was performed on a regular basis. It was also concluded that the derivate of cylindrospermopsin could also exist in the form of a pair of tautomers because of the fact that the uracil ring’s vinylic proton was not identified during the application of the H NMR technique as shown in figure 2. However, as every sample of 7-deoxy-cylindrospermopsin (2) was observed the incidence of the uracil group (4) was confirmed by examining the absorbance maximum (ÃŽ »max). Even though, the measurement of approximate quantity was not possible, it was evident that as a mixture of compounds the natural material indeed existed. The discovery of the 7-epi-cylindrospermopsin took place in 20 02 and it was originally established that it was synthesized with Aphanizomenon ovalisporum. The approximation of cylindrospermopsin’s relative stereochemistry was made by considering the unusualtautomer enol presence of the uracil D ring. To explain the concept, uracil D as described in structure 6 is a intramolecularly hydrogen linked to a nitrogen terminus of the guanidine group. The NMR evidence was made to be the basis of the product correlation which understandably led the research participants to conclude that structure 7 was the most appropriate and relevant description of cylindrospermopsin (1).