Senko Dmitry A, Timofeev Nikita D, Kasheverov Igor E, Ivanov Igor A
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, 117997, Russia.
Lomonosov Moscow State University, Moscow, 119991, Russia.
Amino Acids. 2021 May;53(5):665-671. doi: 10.1007/s00726-021-02973-1. Epub 2021 Apr 3.
Protected 4-carboxyoxazolidines and thiazolidines (pseudoprolines) are derivatives of serine, threonine or cysteine amino acids. Such compounds are used in peptide synthesis among the other protected amino acids. They are usually practiced when a peptide sequence is readily aggregating during synthesis due to their ability to disrupt secondary structure formation. Such compounds are usually applied as dipeptides. In present work Fmoc-protected pseudoprolines were synthesized and applied in peptide synthesis not as dipeptides but as individual amino acids. Different acylation protocols and amino acids were tested to acylate pseudoprolines. Several "difficult" peptides were synthesized to confirm the efficacy of such constructions. It was shown that pseudoprolines could be easily synthesized and used in automated or manual synthesis not as dipeptides but as ordinary amino acids.
受保护的4-羧基恶唑烷和噻唑烷（假脯氨酸）是丝氨酸、苏氨酸或半胱氨酸氨基酸的衍生物。这类化合物与其他受保护的氨基酸一起用于肽合成。当肽序列在合成过程中由于其破坏二级结构形成的能力而容易聚集时，通常会使用它们。这类化合物通常以二肽形式使用。在本工作中，合成了Fmoc保护的假脯氨酸，并将其作为单个氨基酸而非二肽应用于肽合成。测试了不同的酰化方案和氨基酸对假脯氨酸进行酰化。合成了几种“难合成”的肽以确认此类结构的有效性。结果表明，假脯氨酸可以很容易地合成，并用于自动化或手动合成中，不是作为二肽，而是作为普通氨基酸。
