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Dr. Karel Hernández Dr. Jesús Joglar Dr. Jordi Bujons Dr. Teodor Parella Prof. Dr. Pere Clapés 《Angewandte Chemie (International ed. in English)》2018,57(14):3583-3587
Pyruvate‐dependent aldolases exhibit a stringent selectivity for pyruvate, limiting application of their synthetic potential, which is a drawback shared with other existing aldolases. Structure‐guided rational protein engineering rendered a 2‐keto‐3‐deoxy‐l ‐rhamnonate aldolase variant, fused with a maltose‐binding protein (MBP‐YfaU W23V/L216A), capable of efficiently converting larger pyruvate analogues, for example, those with linear and branched aliphatic chains, in aldol addition reactions. Combination of these nucleophiles with N‐Cbz‐alaninal (Cbz=benzyloxycarbonyl) and N‐Cbz‐prolinal electrophiles gave access to chiral building blocks, for example, derivatives of (2S,3S,4R)‐4‐amino‐3‐hydroxy‐2‐methylpentanoic acid (68 %, d.r. 90:10) and the enantiomer of dolaproine (33 %, d.r. 94:6) as well as a collection of unprecedented α‐amino acid derivatives of the proline and pyrrolizidine type. Conversions varied between 6–93 % and diastereomeric ratios from 50:50 to 95:5 depending on the nucleophilic and electrophilic components. 相似文献
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Cover Picture: Catalyst‐Enabled Site‐Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors (Angew. Chem. Int. Ed. 17/2018) 下载免费PDF全文
Dr. Daisuke Uraguchi Ryo Shibazaki Naoya Tanaka Kohei Yamada Dr. Ken Yoshioka Prof. Dr. Takashi Ooi 《Angewandte Chemie (International ed. in English)》2018,57(17):4431-4431