Research Computing Center, The University of North Carolina, Chapel Hill, North Carolina 27599-3420, United States.
J Phys Chem Lett. 2020 Oct 15;11(20):8690-8696. doi: 10.1021/acs.jpclett.0c02144. Epub 2020 Sep 29.
Homochirality is a common feature of amino acids and carbohydrates, and its origin is still unknown. Meanwhile, right-handed helices are ubiquitous in nature. Are these two phenomena intrinsically correlated? Here, we propose that homochirality of amino acids and nucleotide sugars originated from the handedness of helices. We show that right-handed 3-helix and α-helix favor the l-chiral form for amino acids, but for deoxyribose sugars, right-handed helices prefer the d-chiral form instead. Our analyses unveil strong cooperativity effects dominated by electrostatic interactions. This work not only resolves the mystery of homochirality by providing a unified explanation for the origin of homochirality in proteins and DNA using helical secondary structures as the root cause but also ratifies the , in which the chirality of a higher hierarchy dictates that of lower ones. Possible applications of this work to asymmetric synthesis and macromolecular assembly are discussed.
手性是氨基酸和碳水化合物的共同特征，其起源仍然未知。同时，自然界中普遍存在右手螺旋。这两种现象是否内在相关？在这里，我们提出氨基酸和核苷酸糖的手性起源于螺旋的手性。我们表明，右手 3 螺旋和α螺旋有利于氨基酸的 l-手性形式，但对于脱氧核糖糖，右手螺旋更喜欢 d-手性形式。我们的分析揭示了由静电相互作用主导的强协同效应。这项工作不仅通过将螺旋二级结构作为根本原因，为蛋白质和 DNA 中手性起源提供了统一的解释，从而解决了手性的奥秘，而且还证实了在更高层次的手性决定了较低层次的手性。讨论了这项工作在手性合成和大分子组装中的可能应用。
