pH-Responsive Aminoproline-Containing Collagen Triple Helices

被引：31

作者：

Egli, Jasmine ^{[1
]}

Siebler, Christiane ^{[1
]}

Maryasin, Boris ^{[2
,3
]}

Erdmann, Roman S. ^{[1
]}

Bergande, Cedric ^{[1
]}

Ochsenfeld, Christian ^{[2
,3
]}

Wennemers, Helma ^{[1
]}

机构：

[1] ETH, Lab Organ Chem, Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

[2] Univ Munich LMU, Chair Theoret Chem, Dept Chem, Butenandtstr 7, D-81377 Munich, Germany

[3] Univ Munich LMU, Ctr Integrated Prot Sci CIPSM, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 33期

基金：

瑞士国家科学基金会;

关键词：

conformation analysis; density functional calculations; helical structures; protein folding; protein structures; PEPTIDE-BOND ISOMERIZATION; CONFORMATIONAL STABILITY; GAUCHE PREFERENCE; MIMETIC PEPTIDES; BASIS-SETS; DESIGN; RING; HYDROXYPROLINE; STABILIZATION; SUBSTITUENTS;

D O I：

10.1002/chem.201701134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(4S)-and (4R)-configured aminoproline (Amp) residues were used as pH-responsive probes to tune the thermal stability of collagen triple helices in acidic and basic environments. The different steric and stereoelectronic properties of amino versus ammonium groups lead to a switch of the ring pucker of Amp upon changing the pH. The choice of the position of Amp within collagen model peptides (CMPs) as well as the absolute configuration at C(4) of the pH-responsive probe allows for tuning of the stability of Amp-containing collagen triple helices over a broad range. Comparative quantum chemical calculations on the steric and stereoelectronic effects of amino and ammonium groups versus fluorine, hydroxy, chlorine, and methyl substituents support the experimental findings. The research also shows that substitution of the naturally occurring hydroxy group in collagen by electron-withdrawing groups with a larger hydration shell than that of the hydroxy group is not tolerated.

引用

页码：7938 / 7944

页数：7

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