Enantioselective, Chromatography-Free Synthesis of β~3-Amino Acids with Natural and Unnatural Side Chains

Thibaud Gerfaud; Ying-Ling Chiang; Imants Kreituss

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Enantioselective, Chromatography-Free Synthesis of β~3-Amino Acids with Natural and Unnatural Side Chains

机译：具有天然和非天然侧链的β〜3-氨基酸的对映体，无色谱合成

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β~3-Amino acids are key components of some pharmaceuticals, excellent surrogates for metabolically labile α-amino acids, and building blocks for chiral heterocycles. Unfortunately they are not easily accessible in enantiomerically pure form, especially when possessing unnatural side chains. A flexible, chromatography-free process for the synthesis of enantiopure β~3-amino acids possessing natural and unnatural side chains is described. The procedure uses inexpensive starting materials and reagents and offers a good alternative to the hazardous and expensive Arndt-Eistert homologation of enantiopure α-amino acids. Its utility has been demonstratedwith the preparative scale synthesis of two valuable β~3-amino acids possessing unnatural side chains.

机译：β〜3-氨基酸是某些药物的关键成分，是对代谢不稳定的α-氨基酸的出色替代物，并且是手性杂环的结构单元。不幸的是，它们不容易以对映体纯的形式获得，特别是当具有不自然的侧链时。描述了一种灵活的无色谱方法，用于合成具有天然和非天然侧链的对映纯β〜3-氨基酸。该方法使用廉价的起始原料和试剂，为对映纯α-氨基酸的危险且昂贵的Arndt-Eistert同源提供了很好的替代方法。它的实用性已通过制备规模上合成的两个具有非天然侧链的有价值的β〜3-氨基酸得到了证明。

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《Organic process research & development》 |2012年第4期|共10页
作者
Thibaud Gerfaud; Ying-Ling Chiang; Imants Kreituss;
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1. Enantioselective, Chromatography-Free Synthesis of β~3-Amino Acids with Natural and Unnatural Side Chains [J] . Thibaud Gerfaud, Ying-Ling Chiang, Imants Kreituss Organic process research & development . 2012,第4期

机译：具有天然和非天然侧链的β〜3-氨基酸的对映体，无色谱合成
2. Development of novel enantioselective HPLC methods for the determination of the optical purity of Nα-Fmoc/Boc amino acid derivatives (Nα-PADs) of natural and unnatural amino acids: an analytical strategy for the key starting materials of therapeutic peptides [J] . Yagnakirankumar Komaravolu, Venugopala Rao Dama, Thirumala Chary Maringanti Analytical methods . 2018,第21期

机译：用于测定天然和非天然氨基酸的Nα-Fmoc/ Boc氨基酸衍生物（Nα-PADs）光学纯度的新型对映选择性HPLC方法的开发：治疗性肽类关键原料的分析策略
3. Development of novel enantioselective HPLC methods for the determination of the optical purity of N alpha-Fmoc/Boc amino acid derivatives (N alpha-PADs) of natural and unnatural amino acids: an analytical strategy for the key starting materials of therapeutic peptides [J] . Komaravolu Yagnakirankumar, Dama Venugopala Rao, Maringanti Thirumala Chary Analytical methods . 2018,第21期

机译：新型对映选择性HPLC方法的开发，用于测定天然和非天然氨基酸的Nα-FMOC / BOC氨基酸衍生物（Nα垫）的光学纯度：治疗肽关键原料的分析策略
4. Synthesis of Unnatural α-Amino Acids by PhotoinducedDecarboxylative Radical Addition to Dehydroamino Acids [C] . Mugen Yamawaki, Akiko Asano, Yasuharu Yoshimi 日本化学会春季年会 . 2020

机译：用光致癸酸酯基于脱氢氨基酸的光致α-氨基酸的合成
5. Protein design using unnatural amino acids with fluorinated side chains. [D] . Bilgicer, Zihni Basar. 2005

机译：使用带有氟化侧链的非天然氨基酸进行蛋白质设计。
6. Alpha-helix stabilization by natural and unnatural amino acids with alkyl side chains. [O] . P C Lyu, J C Sherman, A Chen, 1991

机译：通过具有烷基侧链的天然和非天然氨基酸稳定α-螺旋。
7. THE DESIGN AND SYNTHESIS OF NOVEL UNNATURAL AMINO ACIDS AND THE DESIGN AND SYNTHESIS OF PEPTIDES PEPTIDOMIMETICS CONTAINING UNNATURAL AMINO ACIDS FOR THE STUDY OF G-PROTEIN COUPLED RECEPTORS [O] . Liu Zhihua 2010

机译：新型非天然氨基酸的设计与合成以及含非天然氨基酸的肽和肽亚型的设计与合成，用于研究G蛋白偶联受体

Enantioselective, Chromatography-Free Synthesis of β~3-Amino Acids with Natural and Unnatural Side Chains

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