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立体化学对α-烷酰基取代的苏氨酸和丝氨酸两亲分子在气-水界面单层特性的影响。

Influence of Stereochemistry on the Monolayer Characteristics of -alkanoyl-Substituted Threonine and Serine Amphiphiles at the Air-Water Interface.

作者信息

Brezesinski G, Strati F, Rudert R, Vollhardt D

机构信息

Institute for Applied Dermatopharmacy, Martin Luther University Halle-Wittenberg, Weinbergweg 23, D-06120 Halle, Germany.

Section of Chemical Information Systems, University of Ulm, D-89081 Ulm, Germany.

出版信息

Langmuir. 2021 Aug 3;37(30):9069-9077. doi: 10.1021/acs.langmuir.1c01108. Epub 2021 Jul 21.

DOI:10.1021/acs.langmuir.1c01108
PMID:34288683
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8397399/
Abstract

Thermodynamic and structural properties of the -alkanoyl-substituted α-amino acids threonine and serine, differing only by one CH group in the head group, are determined and compared. Detailed characterization of the influence of stereochemistry proves that all enantiomers form an oblique monolayer lattice structure whereas the corresponding racemates build orthorhombic lattice structures due to dominating heterochiral interactions, except -C16-dl-serine-ME as first example of dominating homochiral interactions in a racemic mixture of -alkanoyl-substituted α-amino acids. In all cases, the liquid expanded-liquid condensed (LE/LC) transition pressure of the racemic mixtures is above that of the corresponding enantiomers. Phase diagrams are proposed. Using the program Hardpack to predict tilt angles and cross-sectional area of the alkyl chains shows reasonable agreement with the experimental grazing incidence X-ray diffraction (GIXD) data.

摘要

研究并比较了仅在头基中相差一个-CH基团的α-链烷酰基取代的苏氨酸和丝氨酸的热力学和结构性质。对立体化学影响的详细表征表明，所有对映体均形成倾斜的单层晶格结构，而相应的外消旋体由于占主导的异手性相互作用而形成正交晶格结构，但-C16-dl-丝氨酸-ME除外，它是α-链烷酰基取代的α-氨基酸外消旋混合物中占主导的同手性相互作用的首个实例。在所有情况下，外消旋混合物的液-扩-液-凝（LE/LC）转变压力均高于相应对映体的转变压力。提出了相图。使用Hardpack程序预测烷基链的倾斜角和横截面积，结果与实验掠入射X射线衍射（GIXD）数据显示出合理的一致性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcca/8397399/44ee7bb8257d/la1c01108_0009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcca/8397399/44ee7bb8257d/la1c01108_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcca/8397399/c21db11575e9/la1c01108_0002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcca/8397399/13e5e3ddefdb/la1c01108_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcca/8397399/12583320a85f/la1c01108_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcca/8397399/44ee7bb8257d/la1c01108_0009.jpg

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引用本文的文献

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本文引用的文献

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2
Special features of monolayer characteristics of N-alkanoyl substituted threonine amphiphiles.N-酰基取代苏氨酸两亲物单层特性的特殊性质。
Phys Chem Chem Phys. 2018 Dec 19;21(1):96-103. doi: 10.1039/c8cp06481d.
3
Langmuir Nanoarchitectonics from Basic to Frontier.从基础到前沿的朗缪尔纳诺构筑学
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Chiral Cyclobutane β-Amino Acid-Based Amphiphiles: Influence of Cis/Trans Stereochemistry on Condensed Phase and Monolayer Structure.手性环丁烷 β-氨基酸两亲分子：顺/反立体化学对凝聚相和单层结构的影响。
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