New Analogues of Aspergillic Acid Derived from Methionine

1972 ◽  
Vol 50 (5) ◽  
pp. 543-549 ◽  
Author(s):  
J. C. MacDonald
Keyword(s):  
Amino Acids ◽  
Magnetic Resonance ◽  
Acrylic Acid ◽  
Propionic Acid ◽  
Aspergillus Flavus ◽  
Yeast Extract ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Media Composition

Aspergillus flavus PRL 932 grown on 2% yeast extract plus 1% methionine produced some compounds which, according to their structures, were probably derived in part or completely from methionine. These included 3-(methylthio)-propionic acid, trans-3-(methylthio)-acrylic acid, and various 1-hydroxy-2(1H)-pyrazinones (HPY) with 2-(methylthio)-ethyl (MTE) substituents. The latter compounds were identified by proton magnetic resonance and mass spectra as 3,6-di-MTE-HPY, 3-MTE-6-isopropyl-HPY, 3-isobutyl-6-MTE-HPY, 3-MTE-6-isobutyl-HPY, and 3-MTE-6-sec-butyl-HPY.Changes in media composition, including supplementation with either L-leucine, L-isoleucine, or L-valine changed the relative amounts of various HPYs produced. The results indicated that amino acids competed as precursors for the biosynthesis of HPYs and that L-leucine and L-isoleucine were utilized more effectively than was L-methionine.

Biosynthesis of arglecin and related compounds

1977 ◽  
Vol 55 (2) ◽  
pp. 165-172 ◽  
Author(s):  
J. C. MacDonald ◽  
G. G. Bishop
Keyword(s):  
Amino Acids ◽  
Magnetic Resonance ◽  
Yeast Extract ◽  
Proton Magnetic Resonance ◽  
Synthetic Medium ◽  
Natural Abundance ◽  
Maximum Production ◽  
Specific Activities ◽  
Related Compounds ◽  
Streptomyces Toxytricini

The requirements for maximum production of arglecin, 3-isobutyl-6-(3-guanidinopropyl)-2(1H)pyrazinone, by Streptomyces toxytricini grown on either yeast extract or synthetic medium, were supplements of L-arginine and L-leucine. The arglecin produced was derived to a major extent from these amino acids, as was shown by comparison of specific activities in 14C-labeling experiments.Various compounds related to arglecin could be synthesized by the organism, and these were isolated and their structures determined primarily by natural-abundance carbon-13 and proton magnetic resonance methods. In old cultures which had produced arglecin, the metabolite 3-isobutyl-6-(3-aminopropyl)-2(1H)pyrazinone was found. In cultures grown on synthetic medium supplemented with L-leucine and L-homoarginine, the metabolite 3-isobutyl-6-(4-guanidinobutyl)-2(1H)pyrazinone was found, and in cultures that had been supplemented with L-norleucine and L-arginine, the metabolite 3-butyl-6-(3-guanidinopropyl)-2(1H)pyrazinone was found.

The preparation of 2-Fluoro-5-nitrobenzonitrile and the proton magnetic resonance spectra of some compounds containing the N-(2-Cyano-4-nitrophenyl) group

1967 ◽  
Vol 20 (8) ◽  
pp. 1663 ◽  
Author(s):  
JFK Wilshire
Keyword(s):  
Amino Acids ◽  
Magnetic Resonance ◽  
Nitro Group ◽  
Proton Magnetic Resonance ◽  
Cyano Group ◽  
Aromatic Nucleus ◽  
Heteroaromatic Compounds ◽  
Magnetic Resonance Spectra

2-Fluoro-5-nitrobenzonitrile, an analogue of 1-fluoro-2,4- dinitrobenzene, in which the 2-nitro group has been replaced by a cyano group, has been prepared and made to react with several amines, amino acids, and NH-heteroaromatic compounds. The proton magnetic resonance spectra of some of the resultant N-(2-cyano-4-nitrophenyl) derivatives were compared with the spectra of the corresponding N-(2,4- dinitrophenyl) derivatives and furnish further evidence that the ortho nitro group of the latter derivatives is rotated out of the plane of the aromatic nucleus.

Proton magnetic resonance in aliphatic α-amino acids

1972 ◽  
Vol 17 (4) ◽  
pp. 623-625 ◽  
Author(s):  
S. Ratković
Keyword(s):  
Amino Acids ◽  
Magnetic Resonance ◽  
Proton Magnetic Resonance

Mass spectra and proton magnetic resonance spectra of some tetrahydroprotoberberine alkaloids

1968 ◽  
Vol 46 (15) ◽  
pp. 2501-2506 ◽  
Author(s):  
C.-Y. Chen ◽  
D. B. MacLean
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Structural Studies ◽  
New Members ◽  
Magnetic Resonance Spectra

The mass spectra and the proton magnetic resonance spectra of tetrahydroprotoberberine alkaloids, oxygenated at the 9- and 10-positions, show marked differences from the spectra of those oxygenated at the 10- and 11-positions. These differences may be useful in structural studies on new members of this group of alkaloids.

Proton magnetic resonance and mass spectrometric studies on derivatives of sodium 2-O-α-D-mannopyranosyl-D-glycerate and related compounds

1969 ◽  
Vol 47 (21) ◽  
pp. 4083-4086 ◽  
Author(s):  
J. N. C. Whyte
Keyword(s):  
Magnetic Resonance ◽  
Methyl Ester ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Red Alga ◽  
Mass Spectrometric ◽  
Derivatives Of ◽  
Related Compounds

The proton magnetic resonance (p.m.r.) and mass spectra of the methyl ester pentaacetate of sodium 2-O-α-D-mannopyranosyl-D-glycerate from the red alga Rhodomela larix are compared to those of related compounds to affirm the assigned structure.

Synthesis of phenethanolamine derivatives with potential β-adrenergic antagonistic activity

1975 ◽  
Vol 28 (5) ◽  
pp. 1023 ◽  
Author(s):  
SJ Pasaribu ◽  
LR Williams
Keyword(s):  
Magnetic Resonance ◽  
Ring Opening ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Antagonistic Activity ◽  
Spectral Studies ◽  
Aryl Ring ◽  
Mass Spectral

The mass spectra of bromonitroacetophenones, intermediates in the synthesis of phenethanolamine derivatives containing a nitro and bromo group in the aryl ring, have been studied. The acetophenones were converted into the corresponding α,β-epoxystyrenes, which were then treated with various amines, and proton magnetic resonance and mass spectral studies were used to confirm the direction of ring opening and purity of the products.

Identification of 1-(1-Cyanocycloalkyl)amines, Intermediates in the Synthesis of Phencyclidine and Its Analogs

1977 ◽  
Vol 60 (1) ◽  
pp. 32-47 ◽  
Author(s):  
Denise R Gagné ◽  
Richard K Pike
Keyword(s):  
Magnetic Resonance ◽  
Qualitative Analysis ◽  
Thin Layer ◽  
Infrared Spectra ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Spectroscopic Techniques

Abstract Eight 1-(1-cyanocycloalkyl)amines are identified by spectroscopic techniques. Their ultraviolet and mass spectra are similar, but proton magnetic resonance and infrared spectra are distinctly different; reference spectra and data are provided. Gas-liquid and thin layer chromatographic systems for their qualitative analysis are discussed.

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