By Wolfgang Steglich (auth.), Prof. Dr. Urs Peter Schlunegger (eds.)
Over the prior few years there was a notable and speedy improvement of recent analytical equipment, 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 concepts have additionally arisen to give a contribution to a transforming into knowing of the connection among chemical constitution and organic task. on the way to discover the various extra attention-grabbing issues of these advancements and purposes, a seminar "From organic task to constitution" used to be geared up 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 style sufficient to wait and speak about many points in their study, specially methodological and technical advancements and their purposes to precise difficulties. members have been brought to non-stop circulate FAB (fast atom bombardment) and its use, for instance, within the genuine 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 adjustments of peptides; and the site of S-S bridges in making a choice on the tertiary constitution of proteins.
Read or Download 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 PDF
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Additional 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
_ .... 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  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  IX Herbicolin  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.
Reprinted with permission from reference 19). individual components which are eluted from the chromatograph are ionized and mass analyzed. The MS/MS combination conceptually works the same way. For a mixture analysis, the ion source produces (M+H) + ions from the molecular species present in the sample. The first mass filter is used to select one of these molecular species and transmit it into the collision chamber. Here, collision activated decomposition (CAD) fragments the molecule and in the third quadrupole, these fragments are individually analyzed to give a daughter ion spectrum.
In vivoincorporation of 14C-Iabeled precursors into surfactin was controlled by hydrolysis (6 N HCI at 110°C for 24 h) . The hydrolysates were analyzed by thin layer chromatography and radioscanning. It was demonstrated that all amino acid components were directly incorporated into the lipopeptide product. [ 14 C] acetate appeared in the fatty acid portion of surfactin. The main component is 3-hydroxy13-methyltetradecanoic acid. In vitro biosynthesis of this lipopeptide was studied in B. subtilis ATCC 21322 which was fermented in the Landy medium .