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恶劣条件下蛋白质氨基酸间不对称性的转移

Transfer of Asymmetry between Proteinogenic Amino Acids under Harsh Conditions.

作者信息

Tarasevych Arkadii V, Vives Thomas, Snytnikov Valeriy N, Guillemin Jean-Claude

机构信息

Boreskov Institute of Catalysis of the Siberian Branch of the Russian Academy of Sciences, pr. Lavrentieva, 5, 630090, Novosibirsk, Russia.

Institut des Sciences Chimiques de Rennes, École Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France.

出版信息

Orig Life Evol Biosph. 2017 Sep;47(3):371-379. doi: 10.1007/s11084-017-9535-4. Epub 2017 Mar 31.

DOI:10.1007/s11084-017-9535-4
PMID:28361302
Abstract

The heating above 400 °C of serine, cysteine, selenocysteine and threonine leads to a complete decomposition of the amino acids and to the formation in low yields of alanine for the three formers and of 2-aminobutyric acid for the latter. At higher temperature, this amino acid is observed only when sublimable α-alkyl-α-amino acids are present, and with an enantiomeric excess dependent on several parameters. Enantiopure or enantioenriched Ser, Cys, Sel or Thr is not able to transmit its enantiomeric excess to the amino acid formed during its decomposition. The presence during the sublimation-decomposition of enantioenriched valine or isoleucine leads to the enantioenrichment of all sublimable amino acids independently of the presence of many decomposition products coming from the unstable derivative. All these studies give information on a potentially prebiotic key-reaction of abiotic transformations between α-amino acids and their evolution to homochirality.

摘要

丝氨酸、半胱氨酸、硒代半胱氨酸和苏氨酸在400℃以上加热会导致氨基酸完全分解,前三种氨基酸会低产率生成丙氨酸,后一种氨基酸会低产率生成2-氨基丁酸。在更高温度下,只有当存在可升华的α-烷基-α-氨基酸时才会观察到这种氨基酸,其对映体过量取决于几个参数。对映体纯或对映体富集的丝氨酸、半胱氨酸、硒代半胱氨酸或苏氨酸无法将其对映体过量传递给其分解过程中形成的氨基酸。在升华分解过程中,对映体富集的缬氨酸或异亮氨酸的存在会导致所有可升华氨基酸的对映体富集,而与许多来自不稳定衍生物的分解产物的存在无关。所有这些研究都提供了关于α-氨基酸之间非生物转化的潜在益生元关键反应及其向同手性进化的信息。

相似文献

1
Transfer of Asymmetry between Proteinogenic Amino Acids under Harsh Conditions.恶劣条件下蛋白质氨基酸间不对称性的转移
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本文引用的文献

1
Mass spectrometry characterization of the thermal decomposition/digestion (TDD) at cysteine in peptides and proteins in the condensed phase.质谱法研究肽和蛋白质在凝聚相中半胱氨酸的热分解/消解(TDD)
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Phenomenon of optical self-purification of chiral non-racemic compounds.手性非外消旋化合物的光学自净化现象。
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Thermal formation of homochiral serine clusters and implications for the origin of homochirality.
同手性丝氨酸簇的热形成及其对同手性起源的影响。
J Am Chem Soc. 2006 Dec 27;128(51):17074-86. doi: 10.1021/ja064617d.
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Formation of sugar-specific reactive intermediates from (13)C-labeled L-serines.由碳-13标记的L-丝氨酸形成糖特异性反应中间体。
J Agric Food Chem. 2000 Mar;48(3):636-41. doi: 10.1021/jf990687a.