Reversed-phase high performance liquid chromatographic separation of diastereomers of β-amino alcohols and microwave assisted synthesis of Marfey's reagent, its chiral variants and diastereomers

Ravi Bhushan; Rajender Kumar

doi:10.1016/j.chroma.2009.01.045

Reversed-phase high performance liquid chromatographic separation of diastereomers of β-amino alcohols and microwave assisted synthesis of Marfey's reagent, its chiral variants and diastereomers

Ravi Bhushan
, Rajender Kumar

Indian Institute of Technology Roorkee

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

28 Scopus citations

Abstract

Ten chiral derivatizing reagents (CDRs) were synthesized by replacing the l-Ala-NH₂ moiety in Marfey's reagent (MR) by seven l-amino acid amides and three l-amino acids employing microwave irradiation (MW) and were characterized. Ten racemic amino alcohols were derivatized with these CDRs under MW. The diastereomers were separated on a reversed-phase C₁₈ column using binary mixtures of acetonitrile with aqueous trifluoroacetic acid (TFA) and triethylammonium phosphate buffer (TEAP). In general, amino acid variants of MR provided better separation of diastereomers in comparison to amino acid amide variants. The method was also found successful for the separation of 20 diastereomers from a mixture.

Original language	English
Pages (from-to)	2592-2596
Number of pages	5
Journal	Journal of Chromatography A
Volume	1216
Issue number	12
DOIs	https://doi.org/10.1016/j.chroma.2009.01.045
State	Published - 20 Mar 2009
Externally published	Yes

Bibliographical note

Funding Information:
The authors are thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India for the award of a junior research fellowship to R.K., to the Alexander von Humboldt Foundation, Bonn, Germany, for donating Knauer HPLC equipment (to R.B. in 2006) and to Professor Hans Brückner, IFZ, University of Giessen, Germany for donating homophenyl alaninol used in the present studies.

Funding

The authors are thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India for the award of a junior research fellowship to R.K., to the Alexander von Humboldt Foundation, Bonn, Germany, for donating Knauer HPLC equipment (to R.B. in 2006) and to Professor Hans Brückner, IFZ, University of Giessen, Germany for donating homophenyl alaninol used in the present studies.

Funders
Alexander von Humboldt-Stiftung
Council of Scientific and Industrial Research, India

Keywords

Amino acid variants
Indirect chiral separation
Marfey's reagent
Microwave assisted synthesis
Reversed-phase high-performance liquid chromatography
β-Amino alcohols

Access to Document

10.1016/j.chroma.2009.01.045

Cite this

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title = "Reversed-phase high performance liquid chromatographic separation of diastereomers of β-amino alcohols and microwave assisted synthesis of Marfey's reagent, its chiral variants and diastereomers",

abstract = "Ten chiral derivatizing reagents (CDRs) were synthesized by replacing the l-Ala-NH2 moiety in Marfey's reagent (MR) by seven l-amino acid amides and three l-amino acids employing microwave irradiation (MW) and were characterized. Ten racemic amino alcohols were derivatized with these CDRs under MW. The diastereomers were separated on a reversed-phase C18 column using binary mixtures of acetonitrile with aqueous trifluoroacetic acid (TFA) and triethylammonium phosphate buffer (TEAP). In general, amino acid variants of MR provided better separation of diastereomers in comparison to amino acid amide variants. The method was also found successful for the separation of 20 diastereomers from a mixture.",

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Reversed-phase high performance liquid chromatographic separation of diastereomers of β-amino alcohols and microwave assisted synthesis of Marfey's reagent, its chiral variants and diastereomers. / Bhushan, Ravi; Kumar, Rajender.
In: Journal of Chromatography A, Vol. 1216, No. 12, 20.03.2009, p. 2592-2596.

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

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AU - Bhushan, Ravi

AU - Kumar, Rajender

N1 - Funding Information: The authors are thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India for the award of a junior research fellowship to R.K., to the Alexander von Humboldt Foundation, Bonn, Germany, for donating Knauer HPLC equipment (to R.B. in 2006) and to Professor Hans Brückner, IFZ, University of Giessen, Germany for donating homophenyl alaninol used in the present studies.

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N2 - Ten chiral derivatizing reagents (CDRs) were synthesized by replacing the l-Ala-NH2 moiety in Marfey's reagent (MR) by seven l-amino acid amides and three l-amino acids employing microwave irradiation (MW) and were characterized. Ten racemic amino alcohols were derivatized with these CDRs under MW. The diastereomers were separated on a reversed-phase C18 column using binary mixtures of acetonitrile with aqueous trifluoroacetic acid (TFA) and triethylammonium phosphate buffer (TEAP). In general, amino acid variants of MR provided better separation of diastereomers in comparison to amino acid amide variants. The method was also found successful for the separation of 20 diastereomers from a mixture.

AB - Ten chiral derivatizing reagents (CDRs) were synthesized by replacing the l-Ala-NH2 moiety in Marfey's reagent (MR) by seven l-amino acid amides and three l-amino acids employing microwave irradiation (MW) and were characterized. Ten racemic amino alcohols were derivatized with these CDRs under MW. The diastereomers were separated on a reversed-phase C18 column using binary mixtures of acetonitrile with aqueous trifluoroacetic acid (TFA) and triethylammonium phosphate buffer (TEAP). In general, amino acid variants of MR provided better separation of diastereomers in comparison to amino acid amide variants. The method was also found successful for the separation of 20 diastereomers from a mixture.

KW - Amino acid variants

KW - Indirect chiral separation

KW - Marfey's reagent

KW - Microwave assisted synthesis

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KW - β-Amino alcohols

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Reversed-phase high performance liquid chromatographic separation of diastereomers of β-amino alcohols and microwave assisted synthesis of Marfey's reagent, its chiral variants and diastereomers

Abstract

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Keywords

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