Nα-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis†,Organic & Biomolecular Chemistry

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Nα-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-07-12 00:00:00 , DOI: 10.1039/c8ob01485j
Eva Schütznerová _{1,

2,

3,

4,

5} , Adam Přibylka _{3,

5,

6,

7,

8} , Viktor Krchňák _{3,

5,

6,

7,

8}

Affiliation

Fmoc-protected N^α-amino acid containing heterocyclic privileged structures, O-(1-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)-L-serine and O-((S)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)-L-serine, were synthesized on the solid phase from simple commercially available building blocks under mild conditions. The amino acid side-chain is composed of tetramic acid, a natural product derived privileged structure. The key transformation was the formation of cyclic enol ethers via nonclassical Wittig olefinations of the esters. Solid-phase synthesis represents a method of choice, particularly for the synthesis of peptides. This route is compatible with traditional Merrifield solid-phase peptide synthesis (SPPS), as documented on the preparation of the pentapeptide Leu-enkephalin amide H-Tyr-Gly-Gly-Phe-Leu-NH₂ with Phe or Tyr replaced by a novel amino acid.

中文翻译：

Ñ ^α含特权结构氨基酸：设计，合成和使用固相肽合成†

Fmoc-保护的Ñ ^α含氮杂环特权结构，α-氨基酸ø - （1-甲基-5-氧代-2,5-二氢- 1 H ^ -吡咯-3-基） -大号-丝氨酸和ø - （（小号）在温和条件下，由简单的市售结构单元在固相上合成了-5-oxo-2,3,5,7a-四氢-1 H-吡咯嗪-7-基）-L-丝氨酸。氨基酸侧链由天然产物衍生的特权结构四酸组成。关键的转变是通过酯的非经典维蒂希烯化反应。固相合成代表一种选择的方法，特别是对于肽的合成。如制备五肽亮氨酸-脑啡肽酰胺H-Tyr-Gly-Gly-Phe-Leu-NH ₂并用新型Phe或Tyr取代五肽所记录的，该路线与传统的Merrifield固相肽合成（SPPS）兼容氨基酸。

更新日期：2018-07-12

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