Einwirkungen von Metallionen auf S�ure-amide und-imide und die der Desaminierung zugrunde liegenden Reaktionsmechanismen unter Mitber�cksichtigung von Ring�ffnungs- und Ringschlu�-Reaktionen

Bamann, Eugen; Münstermann, Harald; Trapmann, Heinz

doi:10.1007/bf00601994

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Über Aminosäure‐Antagonisten, IV Trennung und Bestimmung der Konfigurationen der stereoisomeren N‐Acetyl‐2‐(2′‐cyclohexenyl)glycine

Kemmer

Trowitzsch

1981

Liebigs Ann. Chem.

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On Amino Acid Antagonists, IV I). -Separation and Determination of the Configurations of the Stereoisomeric N-Acetyl-2-(2'-c yclohexenyl)glycinesThe D-( + )-(I-phenylethy1)amides 5 as well as the D-( -)-0-acetyl-a-phenylglycinolamides 7 of the title compounds were separated on silica gel into the four diastereomeric compounds. All attempts failed to hydrolyze 5 and 7 to the corresponding acids. In contrast the diastereomeric D-( -)-N-acetyl-a-phenylglycinol esters 10 which were separated on silica gel were hydrolysed to the optically active acids 3a -d. The absolute configurations at C-2 in 3 were determined by correlation with the saturated glycine derivatives of known stereochemistry. The relative configurations and hence the absolute configurations at C-1' in 3a -d were deduced from the NMR-and CD-spectra and were confirmed by X-ray analysis of 3a. Only the amino acid 3 b with the (2S,l'R)-configuration exhibits biological activity.

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