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• W2095408293 abstract "Die Stereoselektivität der Thioladdition an Dehydrodipeptide in Abhängigkeit von Struktur und Reaktionsbedingungen wurde untersucht. Bei thiolat-katalysierter Addition von Thiolen an die Dehydroalanyl-prolinamide (7–10) wird mit hoher optischer Induktion das D-Cysteinylpeptid gebildet; nahezu keine Induktion wird bei den analogen Dipeptiden mit einer Ester- oder einer Alkoholfunktion (11 bzw. 12), bei umgekehrter Anordnung von Prolin- und Dehydroalanin-Einheit (14) und bei Ersatz der Prolinhälfte durch Alanin (16) oder Valin (17) beobachtet. Als Modell für Additionsreaktionen an Aminoacrylsäuren im Aminosäuremetabolismus wurde die Thioladdition an verschiedene Dehydrovalinverbindungen 21–26 untersucht. Dabei addierten Salicyliden-, p-Nitrosalicyliden- und Pyridoxyliden-dehydrovalinester (22, 23, 26) Thiole 10- bis 30 mal schneller als Dehydrovalin-, N-Acetyldehydrovalin- und N-Benzylidendehydrovalinester (24, 25, 21). On Amino Acids and Peptides, XXVI:I On Dehydroamino Acids, XIV: Biomimetic Experiments on Cysteine Synthesis Addition of SH-Compounds to Dehydroamino Acids The stereoselectivity of thiol addition to dehydrodipeptides was examined under various conditions. Thiolate-catalyzed addition of thiols to dehydroalanyl-prolineamides (7–10) results in formation of D-cysteinyl-peptides with high optical yields. Almost no stereoselectivity is found during addition to the analogous dehydroalanyl-peptides, containing L-proline ester (11) or L-prolinol (12), to the prolyl-dehydroalanine peptide 14, and to dehydroalanylpeptides containing valine (17) or alanine (16) instead of proline. The thiol addition to several dehydrovaline compounds 21 to 26 was investigated as a model for the metabolic addition reactions to aminoacrylic acids. Especially to salicylidene-, p-nitrosalicylidene-, and the pyridoxylidene dehydrovaline esters (22, 23, and 26) thiols were added 10 to 30 times faster than to dehydrovaline-, N-acetyldehydrovaline-, and benzylidenedehydrovaline ester (24, 25, and 21)." @default.
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• W2095408293 date "1978-03-01" @default.
• W2095408293 modified "2023-10-16" @default.
• W2095408293 title "Über Aminosäuren und Peptide, XXVII: Über Dehydroaminosäuren, XIV: Biomimetische Versuche zur Cysteinbildung. Addition von SH‐Verbindungen an Dehydroaminosäuren" @default.
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• W2095408293 doi "https://doi.org/10.1002/cber.19781110325" @default.
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