Faculty of Chemistry and Pharmacy, Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Innrain 52a, 6020, Innsbruck, Austria.
Amino Acids. 2010 Jul;39(2):579-85. doi: 10.1007/s00726-010-0479-5. Epub 2010 Jan 23.
The salt-induced peptide formation reaction has been proposed as a conceivable preliminary to the prebiotic evolution of peptides. In the present paper, the behaviour of arginine is reported for this reaction together with a discussion of the catalytic effects of glycine, and L- and D-histidine. Importantly, the behaviour of the two histidine enantiomers is different. Both histidine enantiomers perform better than glycine in enhancing the yields of arginine dipeptide with L-histidine being more effective than D-histidine. Yields in the presence of histidine are up to 70 times greater than for arginine solutions alone. This compares with 4.2 times higher in the presence of glycine. This difference is most pronounced in the most concentrated (containing 80 mM arginine) reaction solution where arginine has the lowest reactivity. A distinct preference for dimerisation of L-arginine also appears in the 80 mM cases for catalyses of other amino acids. This phenomenon is different from the behaviour of aliphatic amino acids, which display obvious inherent enantioselectivity for the L-stereomers in the SIPF reaction on their own rather than when catalysed by glycine or histidine.
盐诱导的肽形成反应被认为是前生物肽进化的一个合理的前奏。在本文中，报告了精氨酸在该反应中的行为，同时讨论了甘氨酸以及 L-和 D-组氨酸的催化作用。重要的是，两种组氨酸对映体的行为不同。两种组氨酸对映体在增强精氨酸二肽的产率方面都优于甘氨酸，其中 L-组氨酸比 D-组氨酸更有效。在组氨酸存在下的产率比单独存在精氨酸时高 70 倍。与甘氨酸存在时的 4.2 倍相比，这一差异更为明显。在最浓的（含有 80mM 精氨酸）反应溶液中，这种差异最为明显，其中精氨酸的反应性最低。在其他氨基酸的催化作用下，L-精氨酸的二聚化也明显表现出对 L-对映体的偏好。这种现象与脂肪族氨基酸的行为不同，脂肪族氨基酸在 SIPF 反应中单独存在时对 L-立体异构体表现出明显的固有对映选择性，而在甘氨酸或组氨酸催化时则没有。
