Biologically Active Molecules: Identification, by Wolfgang Steglich (auth.), Prof. Dr. Urs Peter Schlunegger

By Wolfgang Steglich (auth.), Prof. Dr. Urs Peter Schlunegger (eds.)

Over the previous few years there was a extraordinary and quick improvement of contemporary analytical tools, and the fields of nuclear magnetic resonance and mass spectrometry were no exception. as well as with the ability to do "more and faster", new leading edge options have additionally arisen to give a contribution to a turning out to be figuring out of the connection among chemical constitution and organic job. on the way to discover many of the extra attention-grabbing issues of these advancements and functions, a seminar "From organic task to constitution" was once prepared from September 5-7, 1988, at Interlaken. The 4 invited audio system, Richard M. Caprioli, Howard R. Morris, Wolfgang Steglich and Dudley H. Williams have been type sufficient to wait and speak about many elements in their study, particularly methodological and technical advancements and their purposes to precise difficulties. individuals have been brought to non-stop circulate FAB (fast atom bombardment) and its use, for instance, within the actual time tracking of biochemical reactions in vitro and in vivo; the structural elucidation of secondary metabolites from fungi; the research of molecule-receptor interactions; the selection of posttranslational alterations of peptides; and the positioning of S-S bridges in opting for the tertiary constitution of proteins.

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Extra info for Biologically Active Molecules: Identification, Characterization and Synthesis Proceedings of a Seminar on Chemistry of Biologically Active Compounds and Modern Analytical Methods, Interlaken, September 5–7, 1988

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0 Fig. " 4'2 0,1 0,2 u U 0 ............ 10 Fraction number 20 0 Fast protein liquid chromatography (FPLC) on Pharmacia Mono Q HR 5/5 of an enzyme fraction activating the amino acid components of surf actin which was prepurified by DE-52 anioJ exchange chromatography. For elution of the proteins a gradient from 0-0,6 M NaCl in 50 mM Tris/HCl buffer, pH = 7,5; 2 mM dithioerythritol was used. Flow rate: 1 ml/min; temperature: 25°C. 36 Table 1 Lipopeptides produced by various microorganisms Name Producer organism Properties and activities Antibiotic, inhibitor of cell wall synthesis I Amphomycin [1] streptomyces canus II Enduracidin [2-5] Streptomyces fungicidicus III Globomycin [6-8] Streptomyces hygroscopicus IV Cyclosporin [9-11] Tolypocladium inflatum Antifungal agent, immunomodulator V Chlamydocin [12-14] Diheterospora chlamydosporia Cytostatic and antitumor agent VI HC-Toxin [15-17] Cochliobolus carbonum race Phytotoxin VII Polymyxin [18 ] Bacillus polymyxa Antibiotic Pseudomonas viscosa Antiviral agent VIII Viscosin [19] IX Herbicolin [20] Erwinia herbicola Antibiotic, highly active against yeasts and filamentous fungi X Cyanoginosin, Microcystin [21,22] Microcystis aeruginosa (Cyanobacterium) Hepatotoxin, acute toxicity to mammals 37 Table 2 Structures of lipopeptides compiled in Table 1 FA = (+l-3-anteisotridecenoic or 3-isododecenoic acid; FA2 = 10methyl-undeca-2-(cis,4(transl-dienoic acid; FA3 = 2-methylamino-3hydroxy-4-methyl-6-octenoic acid; FA = 3-hydroxytetradecanoic acid; Adda = 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid; Dab = 2,4 Ediaminobutyric acid; Dab e = D-erythro-2,3-diaminobutyric acid; Dab = L-threo-2,3-diaminobutyric acid; Pip = D-a-pipecolic acid; Abu = 2-aminobutyric acid; Sar = sarcosin; HyPhg; 2amino-4-hydroxyphenylacetic acid or hydroxyphenylglycine; CHyPhg = 3-chloro- or 3,S-dichloro-HyPhg; Cit = citrulline; End = a(sl-aminoB-4(Rl-(2-imino imidazolidinyll-propionic acid; aThr = allo-threonine; aIle = allo-isoleucine; Me d Ala = N-Methyl-dehydroalanine; B-MeAsp = erythro-B-methyl-D-iso-aspartic acid.

Finally, in a high vacuum environment, the sample concentration chanqes because of evaporation of the liquid. Nevertheless, despite the difficulties, FAB is an excellent ionization technique and is widely used for the mass spectrometric analysis of polar and charqed molecules. Many different liquid matrices have been used in FABMS, although some are tarqeted at samples which contain specific molecular types. Glycerol is commonly used in many cases with additives such as trifluoroacetic acid, salts, solvents and similar types of compounds to enhance overall ion yield and give qood mass spectra.

S. ,. 20 3485 Figure 9. Isotopic distribution of the molecular species of two polypeptides as they would be recorded by FABMS at unit resolution. For the most part, measurements of high molecular weight compounds (>3000 daltons) are made at less than unit resolutio~ in order to maximize the signal intensity. Decreasing the resolution of a magnetic instrument is accomplished by opening up the squrce and collector slits, and as a consequence, more ions are allowed to pass and be recorded. In these measurements, such as that for insulin shown in Figure 10, the gaussian-shaped peak recorded represents the unresolved isotope cluster.

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