席夫碱的非对映选择性烷基化合成脂质非天然fmoc保护α-氨基酸

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2002-07-19 DOI:10.1002/1099-0690(200208)2002:16<2736::AID-EJOC2736>3.0.CO;2-5

Anna?Maria Papini, Elena Nardi, Francesca Nuti, Jacques Uziel, Mauro Ginanneschi, Mario Chelli, Alberto Brandi

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引用次数: 11

摘要

亲脂性增加的多肽可以更容易地穿过细胞膜，并且具有更长的半衰期。由于这些原因，合成对映体纯的fmoc保护的脂质α-氨基酸是一个相关的目标。2-羟基苯胺-3- 1的两个对映体与Gly-OtBu反应产生的希夫碱被一系列长烷基卤化物烷基化。在亲脂底物精心选择的条件下，用反相高效液相色谱法测定非对映异构体过量。(©Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Diastereoselective Alkylation of Schiff Bases for the Synthesis of Lipidic Unnatural Fmoc-Protected α-Amino Acids

Peptides with increased lipophilicity can cross cell membranes more easily and have longer half-life times. For these reasons, the synthesis of enantiomerically pure Fmoc-protected lipidic α-amino acids is a relevant goal. Schiff bases originating from the reaction between the two enantiomers of 2-hydroxypinan-3-one with Gly-OtBu were alkylated with a series of long alkyl halides. Diastereomeric excesses were determined by reversed-phase HPLC, under conditions carefully chosen for such lipophilic substrates. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.