Chiral autoamplification meets dynamic chirality control to suggest nonautocatalytic chemical model of prebiotic chirality amplification

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Chiral autoamplification meets dynamic chirality control to suggest nonautocatalytic chemical model of prebiotic chirality amplification. / Talsi, Evgenii P.; Bryliakova, Anna A.; Ottenbacher, Roman V. et al.

In: Research, Vol. 2019, 4756025, 04.11.2019.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{14c3f75195bf4cf384c2b594bd44b1ee,

title = "Chiral autoamplification meets dynamic chirality control to suggest nonautocatalytic chemical model of prebiotic chirality amplification",

abstract = "Oxidative kinetic resolution of 1-phenylethanol in the presence of manganese complexes, bearing conformationally nonrigid achiral bis-amine-bis-pyridine ligands, in the absence of any exogenous chiral additives, is reported. The only driving force for the chiral discrimination is the small initial enantiomeric imbalance of the scalemic (nonracemic) substrate: the latter dynamically controls the chirality of the catalyst, serving itself as the chiral auxiliary. In effect, the ee of 1-phenylethanol increases monotonously over the reaction course. This dynamic control of catalyst chirality by the substrate has been unprecedented; a consistent kinetic model for this process is presented. The reported catalyzed substrate self-enantioenrichment mechanism is discussed in relation to the problem of prebiotic chirality amplification.",

author = "Talsi, {Evgenii P.} and Bryliakova, {Anna A.} and Ottenbacher, {Roman V.} and Rybalova, {Tatyana V.} and Bryliakov, {Konstantin P.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 Evgenii P. Talsi et al.",

year = "2019",

month = nov,

day = "4",

doi = "10.34133/2019/4756025",

language = "English",

volume = "2019",

journal = "Research",

issn = "2639-5274",

publisher = "American Association for the Advancement of Science",

}

RIS

TY - JOUR

T1 - Chiral autoamplification meets dynamic chirality control to suggest nonautocatalytic chemical model of prebiotic chirality amplification

AU - Talsi, Evgenii P.

AU - Bryliakova, Anna A.

AU - Ottenbacher, Roman V.

AU - Rybalova, Tatyana V.

AU - Bryliakov, Konstantin P.

PY - 2019/11/4

Y1 - 2019/11/4

N2 - Oxidative kinetic resolution of 1-phenylethanol in the presence of manganese complexes, bearing conformationally nonrigid achiral bis-amine-bis-pyridine ligands, in the absence of any exogenous chiral additives, is reported. The only driving force for the chiral discrimination is the small initial enantiomeric imbalance of the scalemic (nonracemic) substrate: the latter dynamically controls the chirality of the catalyst, serving itself as the chiral auxiliary. In effect, the ee of 1-phenylethanol increases monotonously over the reaction course. This dynamic control of catalyst chirality by the substrate has been unprecedented; a consistent kinetic model for this process is presented. The reported catalyzed substrate self-enantioenrichment mechanism is discussed in relation to the problem of prebiotic chirality amplification.

AB - Oxidative kinetic resolution of 1-phenylethanol in the presence of manganese complexes, bearing conformationally nonrigid achiral bis-amine-bis-pyridine ligands, in the absence of any exogenous chiral additives, is reported. The only driving force for the chiral discrimination is the small initial enantiomeric imbalance of the scalemic (nonracemic) substrate: the latter dynamically controls the chirality of the catalyst, serving itself as the chiral auxiliary. In effect, the ee of 1-phenylethanol increases monotonously over the reaction course. This dynamic control of catalyst chirality by the substrate has been unprecedented; a consistent kinetic model for this process is presented. The reported catalyzed substrate self-enantioenrichment mechanism is discussed in relation to the problem of prebiotic chirality amplification.

UR - http://www.scopus.com/inward/record.url?scp=85078782358&partnerID=8YFLogxK

U2 - 10.34133/2019/4756025

DO - 10.34133/2019/4756025

M3 - Article

C2 - 31922134

AN - SCOPUS:85078782358

VL - 2019

JO - Research

JF - Research

SN - 2639-5274

M1 - 4756025

ER -

ID: 22621716