Stereoselectivity of formation of monoterpene – Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives

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Stereoselectivity of formation of monoterpene – Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives. / Marenin, K. S.; Gatilov, Yu V.; Agafontsev, A. M. et al.

In: Steroids, Vol. 117, 01.01.2017, p. 112-119.

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

BibTeX

@article{ed2ee119168c43e7828c06b9fb9e4e23,

title = "Stereoselectivity of formation of monoterpene – Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives",

abstract = "Reaction of nitrosochlorides of natural monoterpene hydrocarbons (+)-3-carene and (−)-α-pinene with L-amino acids and their methyl esters results in stereoselective formation of terpene–amino acids hybrids, which belong to the series of α-substituted amino oximes. The reaction with an excess of racemic DL-amino acids and their derivatives induces partial resolution of the amino acid components and formation of the diastereomeric mixtures of the terpene–amino acids hybrids, with diastereomeric excess varying from 0 to 100%.",

keywords = "(+)-3-Carene, (−)-α-Pinene, Amino acids, Diastereoselectivity, Nitroso chlorides, Magnetic Resonance Spectroscopy, Amino Acids/chemistry, Stereoisomerism, Monoterpenes/chemistry, Terpenes/chemistry, COORDINATION CHEMISTRY, ZN-II, NATURAL MONOTERPENES, CRYSTAL-STRUCTURES, ALDEHYDES, H2L1, (+)-3-CARENE, BINUCLEAR COMPLEXES, (-)-alpha-Pinene, LIGANDS, II COMPLEXES",

author = "Marenin, {K. S.} and Gatilov, {Yu V.} and Agafontsev, {A. M.} and Tkachev, {A. V.}",

year = "2017",

month = jan,

day = "1",

doi = "10.1016/j.steroids.2016.09.016",

language = "English",

volume = "117",

pages = "112--119",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier Science Inc.",

}

RIS

TY - JOUR

T1 - Stereoselectivity of formation of monoterpene – Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives

AU - Marenin, K. S.

AU - Gatilov, Yu V.

AU - Agafontsev, A. M.

AU - Tkachev, A. V.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Reaction of nitrosochlorides of natural monoterpene hydrocarbons (+)-3-carene and (−)-α-pinene with L-amino acids and their methyl esters results in stereoselective formation of terpene–amino acids hybrids, which belong to the series of α-substituted amino oximes. The reaction with an excess of racemic DL-amino acids and their derivatives induces partial resolution of the amino acid components and formation of the diastereomeric mixtures of the terpene–amino acids hybrids, with diastereomeric excess varying from 0 to 100%.

AB - Reaction of nitrosochlorides of natural monoterpene hydrocarbons (+)-3-carene and (−)-α-pinene with L-amino acids and their methyl esters results in stereoselective formation of terpene–amino acids hybrids, which belong to the series of α-substituted amino oximes. The reaction with an excess of racemic DL-amino acids and their derivatives induces partial resolution of the amino acid components and formation of the diastereomeric mixtures of the terpene–amino acids hybrids, with diastereomeric excess varying from 0 to 100%.

KW - (+)-3-Carene

KW - (−)-α-Pinene

KW - Amino acids

KW - Diastereoselectivity

KW - Nitroso chlorides

KW - Magnetic Resonance Spectroscopy

KW - Amino Acids/chemistry

KW - Stereoisomerism

KW - Monoterpenes/chemistry

KW - Terpenes/chemistry

KW - COORDINATION CHEMISTRY

KW - ZN-II

KW - NATURAL MONOTERPENES

KW - CRYSTAL-STRUCTURES

KW - ALDEHYDES

KW - H2L1

KW - (+)-3-CARENE

KW - BINUCLEAR COMPLEXES

KW - (-)-alpha-Pinene

KW - LIGANDS

KW - II COMPLEXES

UR - http://www.scopus.com/inward/record.url?scp=85006753312&partnerID=8YFLogxK

U2 - 10.1016/j.steroids.2016.09.016

DO - 10.1016/j.steroids.2016.09.016

M3 - Article

C2 - 27693094

AN - SCOPUS:85006753312

VL - 117

SP - 112

EP - 119

JO - Steroids

JF - Steroids

SN - 0039-128X

ER -

ID: 10318133