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- W2000790541 abstract "Aminosäure-N-carbonsäure-anhydride (NCAs) (2,5-Oxazolidindione) 1 lassen sich mittels 2-Nitrobenzolsulfenylchlorid und Triäthylamin unterhalb 0°C schnell, quantitativ und racemisierungsfrei am Stickstoff sulfenylieren. Vierzehn neue NPS-NCAs (3a–c, e–h, k–q), zum Teil von trifunktionellen Aminosäuren, wurden synthetisiert. Die NPS-NCAs 3a–q, 6–8 sind lagerbeständig und polymerisieren nicht. Sie werden schon durch geringe Mengen an Trialkylaminen, aber auch durch reines Pyridin im Lauf von Stunden racemisiert. Die Racemisierung wurde kinetisch untersucht, und ihr Verlauf wird diskutiert. Die NPS-α-NCAs 3a–q eignen sich nicht zur Peptidsynthese in wäßriger Phase (Schotten-Baumann-Methode) und geben auch bei der Umsetzung mit Aminosäurealkylestern keine guten Resultate. Durch Umsetzung mit N-(Trimethylsily)aminosäureestern (22) lassen sich jedoch NPS-Dipeptide (24) in guten Ausbeuten gewinnen. N-(2-Nitrophenylsulfenyl)-α-amino Acid N-Carboxy Anhydrides (NPS-α-NCAs) α-Amino acid N-carboxy anhydrides (2,5-oxazolidinediones) 1 undergo substitution at the nitrogen atom rapidly, quantitatively and without racemization upon treatment with 2-nitrobenzenesulfenyl chloride and triethylamine below 0°C. Fourteen new NPS-α-NCAs (3a–c, e–h, k–q), some of them derived from trifunctional amino acids, were synthesized. The NPS-α-NCAs 3a–q, 6–8 can be stored without decomposition and they do not poly-merize. They undergo rapid racemization in the presence of small quantities of trialkylamines or pure pyridine. The racemization is investigated kinetically and the results are discussed. The NPS-α-NCAs 3a–q are not suitable for peptide synthesis in water-containing systems and give only low yields of NPS-dipeptides upon treatment with amino acid alkyl esters. Good yields of NPS-dipeptides 24 or free dipeptides are obtained by treatment of the NPS-α-NCAs with N-(trimethylsilyl)amino acid trimethylsilyl esters 22." @default.
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- W2000790541 date "1974-11-01" @default.
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- W2000790541 title "<i>N</i> ‐(2‐Nitrophenylsulfenyl)‐α‐aminosäure‐ <i>N</i> ‐carbonsäure‐anhydride" @default.
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- W2000790541 doi "https://doi.org/10.1002/cber.19741071108" @default.
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