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手性,完全伸展的螺旋肽。

Chiral, fully extended helical peptides.

机构信息

ICB, Padova Unit, CNR, Department of Chemistry, University of Padova, via Marzolo 1, 35131 Padua, Italy.

出版信息

Amino Acids. 2011 Aug;41(3):629-41. doi: 10.1007/s00726-011-0839-9. Epub 2011 Feb 4.

DOI:10.1007/s00726-011-0839-9
PMID:21293888
Abstract

The synthesis of the N-protected (blocked) homo-peptide esters from the chiral C(α)-ethyl, C(α)-n-pentylglycine was performed in solution to the hexapeptide level. The conformational propensity exhibited by these oligomers in chloroform solution and in the crystal state was assessed by use of FTIR absorption, NMR, and X-ray diffraction. The results indicated that fully extended helical structures (2.0(5)-helices) are overwhelmingly adopted irrespective of the peptide main-chain length. This oligomeric series is of great interest as it is characterized by the longest C ( i )(α) ,…, C ( i+1 )(α) (per residue) separation achievable in the class of chiral, rigid, helical peptide spacers based on α-amino acids.

摘要

从手性 C(α)-乙基、C(α)-正戊基甘氨酸合成 N-保护(封闭)同肽酯,在溶液中进行到六肽水平。通过傅里叶变换红外吸收、核磁共振和 X 射线衍射评估这些低聚物在氯仿溶液和晶体状态下的构象倾向。结果表明,无论肽主链长度如何,完全伸展的螺旋结构(2.0(5)-螺旋)都被广泛采用。该低聚物系列非常有趣,因为它的特点是在基于α-氨基酸的手性、刚性、螺旋肽间隔物类中,可以实现最长的 C(i)(α)、…、C(i+1)(α)(每残基)分离。

相似文献

1
Chiral, fully extended helical peptides.手性,完全伸展的螺旋肽。
Amino Acids. 2011 Aug;41(3):629-41. doi: 10.1007/s00726-011-0839-9. Epub 2011 Feb 4.
2
Synthesis, conformational study, and spectroscopic characterization of the cyclic C alpha, alpha-disubstituted glycine 9-amino-9-fluorenecarboxylic acid.环状α,α-二取代甘氨酸9-氨基-9-芴羧酸的合成、构象研究及光谱表征
J Pept Sci. 1999 Feb;5(2):61-74. doi: 10.1002/(SICI)1099-1387(199902)5:2<61::AID-PSC173>3.0.CO;2-4.
3
Preferred conformation of peptides rich in Ac8c, a medium-ring alicyclic C (alpha,alpha)-disubstituted glycine.富含Ac8c(一种中环脂环族C(α,α)-二取代甘氨酸)的肽的优选构象。
J Pept Sci. 1996 Jan-Feb;2(1):14-27. doi: 10.1002/psc.43.
4
Synthesis, conformational analysis, and spectroscopic characterization of peptides based on Daf, the first rigid transition-metal receptor, cyclic C(alpha,alpha)-disubstituted glycine.基于首个刚性过渡金属受体——环状C(α,α)-二取代甘氨酸Daf的肽的合成、构象分析及光谱表征。
Biopolymers. 2002 Apr 15;63(5):314-24. doi: 10.1002/bip.10071.
5
(R)-isovaline homo-peptides adopt the left-handed 3(10)-helical structure.(R)-异缬氨酸同型肽采用左手3(10)-螺旋结构。
Pept Res. 1995 Jan-Feb;8(1):6-15.
6
Conformational restriction through C alpha i <--> C alpha i cyclization: Ac12c, the largest cycloaliphatic C alpha,alpha- disubstituted glycine known.通过Cαi <--> Cαi环化实现构象限制:Ac12c,已知最大的脂环族Cα,α-二取代甘氨酸。
Biopolymers. 2000 Feb;53(2):200-12. doi: 10.1002/(SICI)1097-0282(200002)53:2<200::AID-BIP10>3.0.CO;2-L.
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Preferred conformation of peptides based on cycloaliphatic C(alpha,alpha)-disubstituted glycines: 1-amino-cycloundecane-1-carboxylic acid (Ac11c).基于脂环族α,α-二取代甘氨酸的肽的优选构象:1-氨基环十一烷-1-羧酸(Ac11c)。
J Pept Sci. 2000 Nov;6(11):571-83. doi: 10.1002/1099-1387(200011)6:11<571::AID-PSC290>3.0.CO;2-R.
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N-benzhydryl-glycolamide: the first protecting group in peptide synthesis with a strong conformational bias.N-二苯甲基甘醇酰胺:肽合成中首个具有强烈构象偏向性的保护基团。
Biopolymers. 2003;71(1):17-27. doi: 10.1002/bip.10373.
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Preferred 3D-structure of peptides rich in a severely conformationally restricted cyclopropane analogue of phenylalanine.富含苯丙氨酸严重构象受限环丙烷类似物的肽的优选3D结构。
Chemistry. 2005 Dec 16;12(1):251-60. doi: 10.1002/chem.200500865.
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Preferred solution conformation of peptides rich in the lipophilic, chiral, C(alpha)-methylated alpha-amino acid (alpha Me)Aoc.富含亲脂性、手性α-甲基化α-氨基酸(αMe)Aoc的肽的优选溶液构象。
J Pept Sci. 1999 Dec;5(12):547-54. doi: 10.1002/(SICI)1099-1387(199912)5:12<547::AID-PSC221>3.0.CO;2-8.

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