Determination of the Absolute Configurationof Amines

Kerek, F.; Snatzke, Günther

doi:10.1002/anie.197501091

Cited by 6 publications

(1 citation statement)

References 8 publications

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“…To determine the absolute configuration of the amino acid, the related methyl ester H-Aal-OMe was prepared by reaction with diazomethane in methanol and then complexed with Cu(succinimidato) 2 (isopropyl amine) 2 in dichloromethane to produce Cu(succinimidato) 2 (H-Aal-OMe) 2 (8) (Figure 2). The CD spectrum of 8 with its minimum at 600 nm and maximum at 740 nm (Figure 3), when compared with the Cu(succinimidato) complexes of H-D-Trp-OMe and H-L-Trp-OMe [11], clearly confirmed the absolute S-configuration of the amino acid 6 as expected from the enzymatic resolution of the racemate 5.…”

Section: Resultsmentioning

confidence: 54%

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

et al. 2000

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Acetyl-beta-(1-azulenyl)-D,L-alanine has been synthesized in high overall yield by the malonic ester condensation procedure, and the racemate has been enzymatically resolved with acylase I from Aspergillus melleus. The enantiomerically pure L-amino acid is of interest as a blue-colored fluorescent tryptophan analog. The bioactivity data of a heptagastrin analog containing it suggests that the planar aromatic azulene moiety may indeed mimic the tryptophan side chain to some extent, and the spectral properties of the azulene moiety makes beta-(1-azulenyl)-L-alanine of potential value as a UV and fluorescence probe in synthetic peptides, and possibly even in proteins if bioincorporation succeeds with chemically misacylated tRNAs.

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Section: Resultsmentioning

confidence: 54%

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

et al. 2000

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Neue natürliche Aminosäuren

Wagner¹,

Musso²

1983

Angewandte Chemie

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Professor Hans Brochann zum 80. Geburtstag gewidmetDie Mehnahl der ca. 500 heute bekannten natiirlichen Aminosiiuren wurde in den letzten 30 Jahren entdeckt, z. B. bei der Suche nach neuen Antibiotica in der Kulturfliissigkeit von Mikroorganismen oder als Bestandteile dieser Antibiotica, in Pilzen, in Samen, in zahlreichen Pflanzen und Frtichten, auch in Ktlrperfliissigkeiten von Tieren in gebundener Form. Etwa 240 dieser Aminosauren kommen auch frei in der Natur vor, einige nur als Zwischenprodukte des Stoffwechsels. Der vorliegende Beitrag vermittelt einen ifberblick iiber die Entwicklung dieses Gebietes seit 1956, als die letzte Zusammenfassung erschien. K u n und summarisch abgehandelt werden neue ungesiittigte Aminosauren, Cyclopropan-und Cyclobutanaminosiuren, heterocyclische Aminosauren, halogenhaltige Aminosauren, schwefel-, selen-und phosphorhaltige Aminosauren sowie aliphatische AminosBuren. Nur in wenigen Fallen, z. B. bei Betalaminsaure und Muscaflavin, wird die Biosynthese ausfiihrlich erlautert. Historkhe Einleitung

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New Naturally Occurring Amino Acids

Wagner

Musso

1983

Angew. Chem. Int. Ed. Engl.

301

103

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Dedicated to Professor Hans Brockman on the occasion of his 80th birthdayThe majority of the 500 or so naturally occurring amino acids known today were discovered during the last 30 years, for example during the search for new antibiotics in the culture media of microorganisms, or as components of the antibiotics in fungi, seeds, in numerous plants and fruits, and in the body fluids of animals. Some 240 of these amino acids occur free in nature, some only as intermediates in metabolism. This article provides an overview of the developments that have taken place in this area since 1956 when the last review appeared. Summary accounts are presented, dealing with new unsaturated amino acids, cyclopropane-and cyclobutane-amino acids, heterocyclic amino acids, halogen-containing amino acids, sulfur-, selenium-and phosphorus-containing amino acids as well as aliphatic amino acids. In a few cases, e.g. betalamic acid and muscaflavin, the biosynthesis is described in detail. Historical IntroductionIn 1820 glycine was isolated from gelatin hydrolyzates. In the following 100 years the remaining twenty amino acids, which are normally found in proteins, were identified. Only four more were found between 1920 and 1940. With the development of chromatographic methods the number of known naturally occurring amino acids increased rapidly. In 1956 alone over 60 new ones were reported [']. At the moment 500 are known, of which ca. 240 occur free in nature. Still further naturally occurring amino acids are being found eachThe methods of detection and determination of structure have improved so much in recent years that traces of a new fluorescent spot can be discerned in the two dimensional chromatogram of the dansyl derivatives (dansyl = 5-dime- thylamino-l-naphthyl~ulfonyl)[~-~~. Combined GC-MS ofthe N-trifluoroacetyl-methyl ester derivative^'^' confirms that the sample is homogeneous and provides an empirical formula and often a hint as to the structure, which can be corroborated by 'H-and I3C-NMR on a few mg of the amino acid. In particularly difficult cases, such as for example streptolidinis"], an X-ray structure analysis is also necessaryisb1. Nowadays one can determine the enantiomeric purity, usually to better than 0.1%, by gas chromatography of volatile amino acid derivatives on a peptide-ester stationary phase. Equally good results are obtained by chromatography of the free amino acids as diastereoisomeric copper complexes with L-proline on octadecylated silica-gel with aqueous eluents [']. The absolute configuration can be easily determined from CD spectra if a characteristic longwave transition can be produced by making a complextIoal or a dinitrophenyl derivative"ob1. If there are a number of chiral centers the unambiguous assignment of all the isomers is possible through stereospecific synthesis, Unsaturated Amino AcidsThermocymocidin 1 from a thermophilic Eumyces spec i e~~~~,~' ,~~~ and myriocin from the thermophilic fungus Myriococcum albomyce~['~~ are identical, both in their constitution, with a trans double-bon...

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Determination of the Absolute Configurationof Amines

Cited by 6 publications

References 8 publications

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

Synthesis of ?-(1-azulenyl)-L-alanine as a potential blue-colored fluorescent tryptophan analog and its use in peptide synthesis

Neue natürliche Aminosäuren

New Naturally Occurring Amino Acids

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