替考拉宁糖苷配基介质和羧肽酶 Y：寻找低丰度 D-氨基酸和差向异构肽的工具,Chirality

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替考拉宁糖苷配基介质和羧肽酶 Y：寻找低丰度 D-氨基酸和差向异构肽的工具
Chirality ( IF 2.8 ) Pub Date : 2023-03-16 , DOI: 10.1002/chir.23543
Yu-Sheng Sung ₁ , Liudmyla Khvalbota ₂ , Umang Dhaubhadel ₁ , Ivan Špánik ₂ , Daniel W Armstrong ₁

Affiliation

D-氨基酸和差向异构肽/蛋白质可以发挥重要的生物学作用，并对人类年龄相关病理中的蛋白质折叠和寡肽聚集产生不利影响。这引发了人们对游离 D-氨基酸以及肽/蛋白质中的 D-氨基酸及其对人类的影响的兴趣。然而，此类立体异构分析物通常难以捉摸且丰度较低，几乎没有现有的方法能够寻找和识别它们。在这项工作中，我们研究了使用替考拉宁苷元（一种大环抗生素）作为固相萃取的可行性，据报道，它可以强烈保留 D-氨基酸和 C 末端有 D-氨基酸的肽。 SPE）介质。列出了 L-/D-氨基酸和 C 末端修饰的含有 D-氨基酸的肽及其在替考拉宁糖苷配基上的 L-氨基酸专属对应物的 HPLC 保留因子。氨基酸和肽之间的保留曲线差异突出显示了可用于分离的溶剂组成区域。当与羧肽酶 Y 的酶促水解相结合以消除所有 L-氨基酸专有肽时，这种方法特别有用。剩余的具有羧基末端 D-氨基酸的肽随后更容易浓缩和鉴定。当与羧肽酶 Y 的酶促水解相结合以消除所有 L-氨基酸专有肽时，这种方法特别有用。剩余的具有羧基末端 D-氨基酸的肽随后更容易浓缩和鉴定。当与羧肽酶 Y 的酶促水解相结合以消除所有 L-氨基酸专有肽时，这种方法特别有用。其余具有羧基末端 D-氨基酸的肽则更容易浓缩和鉴定。

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Teicoplanin aglycone media and carboxypeptidase Y: Tools for finding low-abundance D-amino acids and epimeric peptides

D-amino acids and epimeric peptides/proteins can play crucial biological roles and adversely affect protein folding and oligopeptide aggregation in age-related pathologies in humans. This has ignited interest in free D-amino acids as well as those incorporated in peptides/proteins and their effects in humans. However, such stereoisomeric analytes are often elusive and in low abundance with few existing methodologies capable of scouting for and identifying them. In this work, we examine the feasibility of using teicoplanin aglycone, a macrocyclic antibiotic, which has been reported to strongly retain D-amino acids and peptides with a D-amino acid on the C-terminus, for use as a solid phase extraction (SPE) medium. The HPLC retention factors of L-/D-amino acids and C-terminus modified D-amino acid-containing peptides and their L-amino acid exclusive counterparts on teicoplanin aglycone are presented. Retention curve differences between amino acids and peptides highlight regions of solvent composition that can be utilized for their separation. This approach is particularly useful when coupled with enzymatic hydrolysis via carboxypeptidase Y to eliminate all L-amino acid exclusive peptides. The remaining peptides with carboxy-terminal D-amino acids are then more easily concentrated and identified.

更新日期：2023-03-16

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