Global S&T Development Trend Analysis Platform of Resources and Environment
DOI | 10.1126/science.abd5680 |
Prebiotic synthesis of cysteine peptides that catalyze peptide ligation in neutral water | |
Callum S. Foden; Saidul Islam; Christian Fernández-García; Leonardo Maugeri; Tom D. Sheppard; Matthew W. Powner | |
2020-11-13 | |
发表期刊 | Science
![]() |
出版年 | 2020 |
英文摘要 | Among amino acids, cysteine is highly reactive as a nucleophile, metal ligand, and participant in redox and radical reactions. These properties make cysteine attractive as a component of prebiotic chemistry, but traditional Strecker synthesis of α-aminonitriles, which can serve as peptide precursors, cannot produce free cysteine. Foden et al. found that a simple acylation of the free amine prevented degradation of cysteine nitrile and enabled synthesis of this cysteine precursor from acetyl dehydroalanine nitrile and a sulfide donor (see the Perspective by Muchowska and Moran). When combined with other proteinogenic α-aminonitriles, acetylcysteine or derivative thiols catalyzed efficient peptide ligation in water. These results highlight how prebiotic synthesis of precursors can also generate function by creating a catalyst for polymerization. Science , this issue p. [865][1]; see also p. [767][2] Peptide biosynthesis is performed by ribosomes and several other classes of enzymes, but a simple chemical synthesis may have created the first peptides at the origins of life. α-Aminonitriles—prebiotic α–amino acid precursors—are generally produced by Strecker reactions. However, cysteine’s aminothiol is incompatible with nitriles. Consequently, cysteine nitrile is not stable, and cysteine has been proposed to be a product of evolution, not prebiotic chemistry. We now report a high-yielding, prebiotic synthesis of cysteine peptides. Our biomimetic pathway converts serine to cysteine by nitrile-activated dehydroalanine synthesis. We also demonstrate that N -acylcysteines catalyze peptide ligation, directly coupling kinetically stable—but energy-rich—α-amidonitriles to proteinogenic amines. This rare example of selective and efficient organocatalysis in water implicates cysteine as both catalyst and precursor in prebiotic peptide synthesis. [1]: /lookup/doi/10.1126/science.abd5680 [2]: /lookup/doi/10.1126/science.abf1698 |
领域 | 气候变化 ; 资源环境 |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/304156 |
专题 | 气候变化 资源环境科学 |
推荐引用方式 GB/T 7714 | Callum S. Foden,Saidul Islam,Christian Fernández-García,et al. Prebiotic synthesis of cysteine peptides that catalyze peptide ligation in neutral water[J]. Science,2020. |
APA | Callum S. Foden,Saidul Islam,Christian Fernández-García,Leonardo Maugeri,Tom D. Sheppard,&Matthew W. Powner.(2020).Prebiotic synthesis of cysteine peptides that catalyze peptide ligation in neutral water.Science. |
MLA | Callum S. Foden,et al."Prebiotic synthesis of cysteine peptides that catalyze peptide ligation in neutral water".Science (2020). |
条目包含的文件 | 条目无相关文件。 |
除非特别说明,本系统中所有内容都受版权保护,并保留所有权利。
修改评论