• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

通过 L-丙氨酸衍生物的烷基化中的构象记忆合成对映体富集的 (R)-C 标记的 2-氨基异丁酸 (Aib)。

Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.

机构信息

School of Chemistry, University of Manchester, Oxford Rd., Manchester M13 9PL, UK.

出版信息

Beilstein J Org Chem. 2011;7:1304-9. doi: 10.3762/bjoc.7.152. Epub 2011 Sep 20.

DOI:10.3762/bjoc.7.152
PMID:22043239
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3201042/
Abstract

The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established.

摘要

库克洛斯基（Kouklovsky）及其同事用于手性选择性烷基化环状 N-萘甲酰基氨基酸衍生物的方法，通过 L-丙氨酸与 (13)CH(3)I 的保留性烷基化，将 (13)C 标记引入 2-氨基异丁酸 (Aib) 的两个对映异位甲基之一。确定了优化产率和对映体纯度的条件，并确定了标记产物的绝对构型。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/b927c06f221f/Beilstein_J_Org_Chem-07-1304-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/eb02f6f79f97/Beilstein_J_Org_Chem-07-1304-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/2c9281138c13/Beilstein_J_Org_Chem-07-1304-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/8a5e5d191573/Beilstein_J_Org_Chem-07-1304-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/df9095abd763/Beilstein_J_Org_Chem-07-1304-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/fb8a1cbea446/Beilstein_J_Org_Chem-07-1304-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/b927c06f221f/Beilstein_J_Org_Chem-07-1304-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/eb02f6f79f97/Beilstein_J_Org_Chem-07-1304-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/2c9281138c13/Beilstein_J_Org_Chem-07-1304-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/8a5e5d191573/Beilstein_J_Org_Chem-07-1304-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/df9095abd763/Beilstein_J_Org_Chem-07-1304-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/fb8a1cbea446/Beilstein_J_Org_Chem-07-1304-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/069d/3201042/b927c06f221f/Beilstein_J_Org_Chem-07-1304-g005.jpg

相似文献

1
Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.通过 L-丙氨酸衍生物的烷基化中的构象记忆合成对映体富集的 (R)-C 标记的 2-氨基异丁酸 (Aib)。
Beilstein J Org Chem. 2011;7:1304-9. doi: 10.3762/bjoc.7.152. Epub 2011 Sep 20.
2
α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers.α-甲基苯甘氨酸通过丙氨酸的不对称 α-芳基化反应得到及其对螺旋 Aib 折叠物构象偏好的影响。
Org Biomol Chem. 2018 Apr 18;16(15):2757-2761. doi: 10.1039/c8ob00551f.
3
Synthesis of [11C-methyl]-alpha-aminoisobutyric acid (AIB).[11C-甲基]-α-氨基异丁酸（AIB）的合成
Nucl Med Biol. 1996 Apr;23(3):263-6. doi: 10.1016/0969-8051(95)02065-9.
4
The Shape of the Simplest Non-proteinogenic Amino Acid α-Aminoisobutyric Acid (Aib).最简单的非蛋白氨基酸α-氨基异丁酸（Aib）的形状。
Chemistry. 2019 Feb 11;25(9):2288-2294. doi: 10.1002/chem.201805038. Epub 2019 Jan 14.
5
Conformational manifold of alpha-aminoisobutyric acid (Aib) containing alanine-based tripeptides in aqueous solution explored by vibrational spectroscopy, electronic circular dichroism spectroscopy, and molecular dynamics simulations.通过振动光谱、电子圆二色光谱和分子动力学模拟探索水溶液中含丙氨酸的三肽的α-氨基异丁酸（Aib）构象集。
J Am Chem Soc. 2007 Oct 31;129(43):13095-109. doi: 10.1021/ja0738430. Epub 2007 Oct 5.
6
Catalytic asymmetric alkylations of ketoimines. Enantioselective synthesis of N-substituted quaternary carbon stereogenic centers by Zr-catalyzed additions of dialkylzinc reagents to aryl-, alkyl-, and trifluoroalkyl-substituted ketoimines.酮亚胺的催化不对称烷基化反应。通过锆催化二烷基锌试剂加成到芳基、烷基和三氟烷基取代的酮亚胺上，对映选择性合成N-取代的季碳立体中心。
J Am Chem Soc. 2008 Apr 23;130(16):5530-41. doi: 10.1021/ja8001343. Epub 2008 Apr 1.
7
Structure-function relationship studies of bovine parathyroid hormone [bPTH(1-34)] analogues containing alpha-amino-iso-butyric acid (Aib) residues.含α-氨基异丁酸（Aib）残基的牛甲状旁腺激素[bPTH(1-34)]类似物的结构-功能关系研究
Biopolymers. 2003 Mar;68(3):437-57. doi: 10.1002/bip.10294.
8
Asymmetric PTC C-alkylation catalyzed by chiral derivatives of tartaric acid and aminophenols. Synthesis Of (R)- and (S)-alpha-methyl amino acids.酒石酸和氨基酚的手性衍生物催化的不对称PTC C-烷基化反应。（R）-和（S）-α-甲基氨基酸的合成。
J Org Chem. 2000 Oct 20;65(21):7041-8. doi: 10.1021/jo000719p.
9
The peptide Z-Aib-Aib-Aib-L-Ala-OtBu.肽 Z-Aib-Aib-Aib-L-Ala-OtBu。
Acta Crystallogr C Struct Chem. 2014 Apr;70(Pt 4):405-7. doi: 10.1107/S2053229614005567. Epub 2014 Mar 21.
10
Conformation of peptides constructed from achiral amino acid residues Aib and DeltaZPhe: computational study of the effect of L/D- Leu at terminal positions.由非手性氨基酸残基Aib和ΔZPhe构建的肽的构象：末端位置L/D-亮氨酸影响的计算研究。
Biopolymers. 2005 Jan;77(1):63-73. doi: 10.1002/bip.20128.

引用本文的文献

1
Inducing a pH-dependent conformational response by competitive binding to Zn of a series of chiral ligands of disparate basicity.通过一系列碱性不同的手性配体与锌的竞争性结合诱导pH依赖性构象响应。
Chem Sci. 2022 Jan 17;13(8):2258-2269. doi: 10.1039/d1sc06812a. eCollection 2022 Feb 23.
2
A tendril perversion in a helical oligomer: trapping and characterizing a mobile screw-sense reversal.螺旋寡聚体中的卷须畸变：捕获并表征移动的螺旋方向反转
Chem Sci. 2017 Apr 1;8(4):3007-3018. doi: 10.1039/c6sc05474a. Epub 2017 Jan 25.
3
Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond.

本文引用的文献

1
Nanometer-range communication of stereochemical information by reversible switching of molecular helicity.
Angew Chem Int Ed Engl. 2010 Sep 10;49(38):6836-9. doi: 10.1002/anie.201001130.
2
N-versus C-terminal control over the screw-sense preference of the configurationally achiral, conformationally helical peptide motif Aib(8)GlyAib(8).N-端与 C-端对非手性、构象螺旋八肽 motif Aib(8)GlyAib(8)的螺旋构象的螺旋手性的控制。
J Am Chem Soc. 2010 Apr 7;132(13):4548-9. doi: 10.1021/ja100662d.
3
Complete mapping of the stereochemical course of retentive deprotonation/alkylation of 1H-benzo[e][1,4]diazepin-2(3H)-ones.1H-苯并[e][1,4]二氮杂卓-2(3H)-酮的立体化学保留性去质子化/烷基化反应的完全映射。
可重新折叠的折叠体：通过单个氢键的缺失或插入实现全局构象转换。
Angew Chem Int Ed Engl. 2016 Feb 5;55(6):2132-6. doi: 10.1002/anie.201510605. Epub 2016 Jan 14.
4
Conformational Switching of a Foldamer in a Multicomponent System by pH-Filtered Selection between Competing Noncovalent Interactions.通过在竞争性非共价相互作用之间进行pH过滤选择，实现多组分体系中折叠体的构象转换。
J Am Chem Soc. 2015 May 27;137(20):6680-91. doi: 10.1021/jacs.5b03284. Epub 2015 May 14.
5
End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching.通过配体诱导的螺旋构象转换实现嘌呤能受体的从头至尾构象通讯。
Nat Chem. 2013 Oct;5(10):853-60. doi: 10.1038/nchem.1747. Epub 2013 Sep 15.
J Am Chem Soc. 2009 Dec 23;131(50):18168-76. doi: 10.1021/ja907507j.
4
Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality.具有氢同位素手性的陨石氨基酸诱导的不对称自催化作用。
Chem Commun (Camb). 2009 Aug 7(29):4396-8. doi: 10.1039/b908754k. Epub 2009 Jun 24.
5
Memory of chirality of tertiary aromatic amides: a simple and efficient method for the enantioselective synthesis of quaternary alpha-amino acids.叔芳酰胺手性记忆：一种对映选择性合成季铵α-氨基酸的简单有效方法。
J Am Chem Soc. 2009 Aug 5;131(30):10711-8. doi: 10.1021/ja9039604.
6
Quantifying end-to-end conformational communication of chirality through an achiral peptide chain.
Angew Chem Int Ed Engl. 2009;48(32):5962-5. doi: 10.1002/anie.200901892.
7
Transmission of stereochemical information over nanometre distances in chemical reactions.化学反应中纳米级距离上立体化学信息的传递。
Chem Soc Rev. 2009 Mar;38(3):817-29. doi: 10.1039/b801639a. Epub 2008 Dec 8.
8
Relaying stereochemistry through aromatic ureas: 1,9 and 1,15 remote stereocontrol.通过芳香脲传递立体化学：1,9和1,15远程立体控制。
Chem Commun (Camb). 2009 Feb 7(5):547-9. doi: 10.1039/b817527f. Epub 2008 Nov 26.
9
Helix persistence and breakdown in oligoureas of metaphenylenediamine: apparent diastereotopicity as a spectroscopic marker of helix length in solution.
J Am Chem Soc. 2008 Nov 12;130(45):15193-202. doi: 10.1021/ja805758v.
10
Conformation and stereodynamics of 2,2'-disubstituted N,N'-diaryl ureas.2,2'-二取代N,N'-二芳基脲的构象与立体动力学
Org Biomol Chem. 2008 Aug 21;6(16):2908-13. doi: 10.1039/b802673d. Epub 2008 Jun 16.