- Asymmetric synthesis of substituted 1-aminocyclopropane1-carboxylic acids via diketopiperazine methodology
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Diketopiperazinespirocyclopropane 12 is prepared in > 98% d.e. via the conjugate addition of a phosphorus ylide to (6S)-N, N′-bis(p-methoxybenzyl)-3-methylenepiperazine-2,5-dione 2. Deprotection and hydrolysis of adduct 12 and subsequent peptide coupling demonstrate the applicability of this methodology to the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acids for incorporation into novel peptides. A model for the high level of diastereofacial selectivity observed in the cyclopropanation reaction is presented. A highly selective asymmetric approach (> 98% d.e.) to (S)-[2,2-2H 2]-1-aminocyclopropane-l-carboxylic acid 29 is also reported via a deuterated sulfur ylide addition to acceptor 2.
- Bunuel, Elena,Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,Savory, Edward D.,Smith, Andrew D.,Vickers, Richard J.,Watkin, David J.
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p. 2531 - 2542
(2007/10/03)
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- Direct dialkylation of peptide nitriles. Application to the synthesis of 1-aminocyclopropane-1-carboxylic acid (Acc)-containing dipeptides
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Several 1-aminocyclopropane-1-carboxylic acid-containing dipeptides (Acc-CP) have been prepared by regioselective dialkylation of peptoids containing α-aminonitriles as C-terminal residues.Regioselective deprotonation of the aminomethylene center using a
- McMath, Andrew R.,Guillaume, Dominique,Aitken, David J.,Husson, Henri-Philippe
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p. 105 - 110
(2007/10/03)
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- Cyclic dipeptides with 1-aminocyclopropane-1-carboxylic acid
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Cyclic dipeptides of the formula cyclo(-Acc-X-), where Acc = 1-aminocyclopropane-1-carboxylic acid, X = Gly, Ala, Val, Leu, Phe or Tyr, were synthesized. The prepared 2,5-piperazinediones showed no proliferative or antiproliferative activity on normal hum
- Kasafirek, Evzen,Moural, Jaroslav,Vinsova, Jarmila,Sturc, Antonin,Taimr, Jan
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p. 941 - 947
(2007/10/03)
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