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Fortschritte Der Chemie Organischer Naturstoffe / Progress by K. Biemann, H. Erdtman, H. Fraenkel-Conrat, O.

By K. Biemann, H. Erdtman, H. Fraenkel-Conrat, O. Hoffmann-Ostenhof, H. Kindl, T. Norin, R. Tschesche, A.B. Turner, F.L. Warren

During the previous 3 many years the natural chemist has turn into in­ creasingly used to exploit increasingly more advanced instrumenta­ tion and actual measurements in lieu of arduous, time-consuming and sometimes ambiguous chemical changes. Mass spectrometry may be the latest, most intricate and most costly addition to this box. In view of the astonishingly fast reputation of nuclear magnetic reso­ nance by means of the natural chemist it really is, looking back, incredible that he has ignored mass spectrometry for one of these very long time. this is often defined, partially, via the complexity of the instrumentation and a few technical shortcomings of the sooner commercially to be had tools yet, to a fair larger quantity, it displays additionally the prejudices opposed to a strategy that was once initially frequently used for quantitative fuel research. The usefulness of mass spectrometry as a qualitative approach in natural chemistry instead of a device for quantitative research used to be progressively more famous in the direction of the tip of the decade. a slightly surprising improvement in the course of the intervening few years to the purpose that now any quite good outfitted smooth natural laboratory is provided with, or at the least has entry to, a number of mass spectrometers appropriate for paintings on natural compounds. in the realm of natural chemistry the procedure has turn into even more very important, if no longer imperative, for the ordinary items chemist whereas its program to man made difficulties is far much less seasoned­ nounced.

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Extra info for Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progres Dans La Chimie Des Substances Organiques Naturelles

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It is rationalized by a transfer of the hydrogen from CIS) to C(2l) or from a hydrogen bearing substituent (CHs or OH) from CIS) to C(21) (8I) . The typical fragmentation pattern (Fig. 9(E) \(J8pQ/p) 7PP ..... f (/i,,) JZIf(IJ) 1711 Fig. 4. Mass spectrum of pieiocarpinine (63). According to THOMAS, ACHENBACH and J. Amer. Chern. Soc. ] BIEMANN. [From: and location of substituents on the basis of the masses of fragments D, E and F (m/e I24 or its analogue). As mentioned earlier, aside from the aspidospermine and aspidofractinine group which both have I9 carbon atoms in the basic skeleton, there exist two other large groups of dihydroindole alkaloids, namely the akuammicine (40) and condylocarpine (44) types (d.

Aspidofractinine. H H H H H H H H C0 2CHa C0 2CHa C0 2CH a C0 2CH a C0 2CH a C0 2CHa C02CH a C0 2CH a C0 2CH a C02CHa C02CH a C0 2CH a R. H H H H H H H H H H H H H H H H CHaO CHaO H Table 3. Alkaloids Related to Aspidofractinine (38). IO-OXO IO,II-dioxo 9-oxide 9-oxide 9-oxide IO-OXO Ll6 16-CHaO 16-CHaO R. " () .... e. ~ Po Z ~ s::... Po CD a en 0 .... ~ CD .... 8 () .... '"0 en til til '" is: (93) (IOS) (87) References K. RIEMANN: 0;/ -( CH 2 CH® ,~ I"N I 2 II ~N® or~ H G (l11/e 130) H (Ill/e 136) Chart 8.

27) does not contain such a hydrogen. The mass spectrum of kopsine does, in fact, not exhibit such a peak. The published data must have been due to a misidentification of the mass of the molecular ion peak. References, pp. 86- 98. ----------------------------------------------Mass Spectrometry of Selected Natural Products. 43 I t is clear that the mass of this conspicuous peak, taken in conjunction with that of the molecular ion, reveals much about the structure of an oxindole or pseudoindoxyl alkaloid; and since they are generally related to naturally occurring indole alkaloids, their complete structure can be easily deduced and corroborated by partial synthesis.

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