5-羧基-甲氨嘧啶-β-氨基酸低聚物。寻找有序性。
Oligomers of a 5-carboxy-methanopyrrolidine β-amino acid. A search for order.
机构信息
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
出版信息
Org Lett. 2010 Dec 3;12(23):5438-41. doi: 10.1021/ol1022917. Epub 2010 Nov 2.
Abstract
CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine β-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C(5)-amide-carbonyls oriented toward the C(4) bridgehead. This highly constrained β-amino acid could prove useful in the ongoing development of well-defined foldamers.
摘要
（1S,4R,5R）-5-顺式-羧酸-2-氮杂双环[2.1.1]己烷（MPCA）的同寡聚物（n = 4、6、8）的 CD 光谱表明其具有有序的二级结构。即使没有内部氢键，四聚体的溶液 NMR、X 射线和计算机分析也表明存在具有反酰胺和 C(5)-酰胺羰基朝向 C(4)桥位的构象。这种高度受限的β-氨基酸在正在进行的定义明确的折叠体的开发中可能很有用。
相似文献
1
Oligomers of a 5-carboxy-methanopyrrolidine β-amino acid. A search for order.5-羧基-甲氨嘧啶-β-氨基酸低聚物。寻找有序性。
Org Lett. 2010 Dec 3;12(23):5438-41. doi: 10.1021/ol1022917. Epub 2010 Nov 2.
2
Water-stable helical structure of tertiary amides of bicyclic β-amino acid bearing 7-azabicyclo[2.2.1]heptane. Full control of amide cis-trans equilibrium by bridgehead substitution.具有 7-氮杂双环[2.2.1]庚烷的双环 β-氨基酸的叔酰胺的水稳定螺旋结构。通过桥接取代完全控制酰胺顺反平衡。
J Am Chem Soc. 2010 Oct 27;132(42):14780-9. doi: 10.1021/ja1017877.
3
Robust trans-amide helical structure of oligomers of bicyclic mimics of β-proline: impact of positional switching of bridgehead substituent on amide cis-trans equilibrium.β-脯氨酸双环模拟物低聚物的稳健反式酰胺螺旋结构：桥头取代基位置转换对酰胺顺反平衡的影响。
J Org Chem. 2014 Jun 6;79(11):5287-300. doi: 10.1021/jo500916j. Epub 2014 May 16.
4
Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds.2,2-二取代吡咯烷-4-羧酸低聚物的二级结构偏好：无法形成分子内氢键的β-肽折叠体
J Am Chem Soc. 2003 Jul 30;125(30):9035-7. doi: 10.1021/ja034561c.
5
Synthesis and structural characterisation as 12-helix of the hexamer of a beta-amino acid tethered to a pyrrolidin-2-one ring.连接到吡咯烷-2-酮环上的β-氨基酸六聚体作为12-螺旋的合成与结构表征。
Chem Commun (Camb). 2006 Dec 21(47):4915-7. doi: 10.1039/b612071g. Epub 2006 Oct 10.
6
Non-hydrogen-bonded secondary structure in beta-peptides: evidence from circular dichroism of (S)-pyrrolidine-3-carboxylic acid oligomers and (S)-nipecotic acid oligomers.β-肽中的非氢键二级结构：来自（S）-脯氨酸-3-羧酸低聚物和（S）-哌啶酸低聚物圆二色性的证据。
Org Lett. 1999 Dec 2;1(11):1717-20. doi: 10.1021/ol9909482.
7
Synthesis of 2,2-disubstituted pyrrolidine-4-carboxylic acid derivatives and their incorporation into beta-peptide oligomers.2,2-二取代吡咯烷-4-羧酸衍生物的合成及其并入β-肽寡聚物中。
J Org Chem. 2005 Apr 29;70(9):3353-62. doi: 10.1021/jo048639z.
8
Synthesis of conformationally constrained 5-fluoro- and 5-hydroxymethanopyrrolidines. Ring-puckered mimics of gauche- and anti-3-fluoro- and 3-hydroxypyrrolidines.构象约束的 5-氟代和 5-羟甲基吡咯烷的合成。顺式和反式 3-氟代和 3-羟甲基吡咯烷的环扭转类似物。
J Org Chem. 2011 May 20;76(10):3626-34. doi: 10.1021/jo200117p. Epub 2011 Apr 18.
9
beta-Pseudopeptide foldamers. The homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac).β-拟肽折叠体。(4R)-(2-氧代-1,3-恶唑烷-4-基)乙酸（D-氧杂环丁烷）的同聚物。
Org Biomol Chem. 2004 Aug 7;2(15):2181-7. doi: 10.1039/B405856A. Epub 2004 Jul 14.
10
Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1]heptadienes using tandem radical addition-homoallylic radical rearrangement.通过串联自由基加成-高烯丙基自由基重排反应从7-氮杂双环[2.2.1]庚二烯立体控制合成红藻氨酸类氨基酸。
J Org Chem. 2005 Oct 28;70(22):8866-76. doi: 10.1021/jo0513865.
引用本文的文献
1
Theoretical and NMR Conformational Studies of β-Proline Oligopeptides With Alternating Chirality of Pyrrolidine Units.具有吡咯烷单元交替手性的β-脯氨酸寡肽的理论与核磁共振构象研究
Front Chem. 2018 Mar 28;6:91. doi: 10.3389/fchem.2018.00091. eCollection 2018.
2
3-Substituted prolines: from synthesis to structural applications, from peptides to foldamers.3-取代脯氨酸：从合成到结构应用，从肽到类肽。
Molecules. 2013 Feb 19;18(2):2307-27. doi: 10.3390/molecules18022307.
本文引用的文献
1
Nature of amide carbonyl--carbonyl interactions in proteins.蛋白质中酰胺羰基 - 羰基相互作用的本质
J Am Chem Soc. 2009 Jun 3;131(21):7244-6. doi: 10.1021/ja901188y.
2
Collagen structure and stability.胶原蛋白结构与稳定性。
Annu Rev Biochem. 2009;78:929-58. doi: 10.1146/annurev.biochem.77.032207.120833.
3
Foldamers with heterogeneous backbones.具有异质主链的折叠体。
Acc Chem Res. 2008 Oct;41(10):1399-408. doi: 10.1021/ar800009n. Epub 2008 Jul 1.
4
Beta-peptidic peptidomimetics.β-肽类拟肽物
Acc Chem Res. 2008 Oct;41(10):1366-75. doi: 10.1021/ar700263g. Epub 2008 Jun 26.
5
The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.由同源蛋白质氨基酸和其他成分组成的β-肽和γ-肽世界。
Chem Biodivers. 2004 Aug;1(8):1111-239. doi: 10.1002/cbdv.200490087.
6
Synthesis of 2,2-disubstituted pyrrolidine-4-carboxylic acid derivatives and their incorporation into beta-peptide oligomers.2,2-二取代吡咯烷-4-羧酸衍生物的合成及其并入β-肽寡聚物中。
J Org Chem. 2005 Apr 29;70(9):3353-62. doi: 10.1021/jo048639z.
7
Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds.2,2-二取代吡咯烷-4-羧酸低聚物的二级结构偏好：无法形成分子内氢键的β-肽折叠体
J Am Chem Soc. 2003 Jul 30;125(30):9035-7. doi: 10.1021/ja034561c.
8
Conformational behavior of beta-proline oligomers.β-脯氨酸低聚物的构象行为。
J Am Chem Soc. 2003 Dec 24;125(51):15855-62. doi: 10.1021/ja036471d.
9
Modification of 1-substituents in the 2-azabicyclo[2.1.1]hexane ring system; approaches to potential nicotinic acetylcholine receptor ligands from 2,4-methanoproline derivatives.2-氮杂双环[2.1.1]己烷环系中1-取代基的修饰；从2,4-亚甲基脯氨酸衍生物制备潜在烟碱型乙酰胆碱受体配体的方法。
J Org Chem. 2003 Nov 28;68(24):9348-55. doi: 10.1021/jo035199n.
10
The polypeptide chain configuration of collagen.胶原蛋白的多肽链构型。
Nature. 1955 Dec 3;176(4492):1062-4. doi: 10.1038/1761062a0.
Zotero 插件