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首页> 外文期刊>Chemistry: A European journal >One-handed helical screw direction of homopeptide foldamer exclusively induced by cyclic α-amino acid side-chain chiral centers
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One-handed helical screw direction of homopeptide foldamer exclusively induced by cyclic α-amino acid side-chain chiral centers

机译：环状α-氨基酸侧链手性中心完全诱导同肽折叠的单手螺旋方向

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摘要

Chiral cyclic α,α-disubstituted amino acids, (3S,4S)- and (3R,4R)-1-amino-3,4-(dialkoxy)cyclopentanecarboxylic acids ((S,S)- and (R,R)-Ac _5c ~(dOR); R: methyl, methoxymethyl), were synthesized from dimethyl L-(+)- or D-(-)-tartrate, and their homochiral homoligomers were prepared by solution-phase methods. The preferred secondary structure of the (S,S)-Ac _5c ~(dOMe) hexapeptide was a left-handed (M) 3 _(10) helix, whereas those of the (S,S)-Ac _5c ~(dOMe) octa- and decapeptides were left-handed (M) α helices, both in solution and in the crystal state. The octa- and decapeptides can be well dissolved in pure water and are more α helical in water than in 2,2,2-trifluoroethanol solution. The left-handed (M) helices of the (S,S)-Ac _5c ~(dOMe) homochiral homopeptides were exclusively controlled by the side-chain chiral centers, because the cyclic amino acid (S,S)-Ac _5c ~(dOMe) does not have an α-carbon chiral center but has side-chain γ-carbon chiral centers.
机译：手性环状α，α-二取代氨基酸，（3S，4S）-和（3R，4R）-1-氨基-3,4-（二烷氧基）环戊烷羧酸（（S，S）-和（R，R）-由酒石酸二甲酯L-（+）-或D-（-）-二甲基丙烯酸酯合成Ac _5c〜（dOR）; R：甲基，甲氧基甲基），并通过溶液相法制备它们的手性均聚物。 （S，S）-Ac _5c〜（dOMe）六肽的首选二级结构是左手（M）3 _（10）螺旋，而（S，S）-Ac _5c〜（dOMe）的二级结构八肽和十肽均为左旋（M）α螺旋，呈溶液状态和晶体状态。与在2,2,2-三氟乙醇溶液中相比，八肽和十肽可以很好地溶解在纯水中，并且在水中的α螺旋更多。 （S，S）-Ac _5c〜（dOMe）同手性同系肽的左手（M）螺旋仅受侧链手性中心控制，因为环状氨基酸（S，S）-Ac _5c〜（ dOMe）不具有α-碳手性中心，但具有侧链γ-碳手性中心。

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