Total synthesis of bistramide A and its 36(Z) isomers: differential effect on cell division, differentiation, and apoptosis

Loïc Tomas; Gustav Boije af Gennäs; Marie Aude Hiebel; Peter Hampson; David Gueyrard; Béatrice Pelotier; Jari Yli-Kauhaluoma; Olivier Piva; Janet M Lord; Peter G Goekjian

doi:10.1002/chem.201102462

Total synthesis of bistramide A and its 36(Z) isomers: differential effect on cell division, differentiation, and apoptosis

Loïc Tomas, Gustav Boije af Gennäs, Marie Aude Hiebel, Peter Hampson, David Gueyrard, Béatrice Pelotier, Jari Yli-Kauhaluoma, Olivier Piva, Janet M Lord, Peter G Goekjian

Inflammation and Ageing

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30 Citations (Scopus)

Abstract

The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product.

Original language	English
Pages (from-to)	7452-66
Number of pages	15
Journal	Chemistry: A European Journal
Volume	18
Issue number	24
DOIs	https://doi.org/10.1002/chem.201102462
Publication status	Published - 11 Jun 2012

Bibliographical note

Keywords

Acetamides
Apoptosis
Cell Division
Cyclization
HL-60 Cells
Humans
Molecular Structure
Pyrans
Spiro Compounds
Stereoisomerism

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10.1002/chem.201102462

Cite this

Tomas, L., Boije af Gennäs, G., Hiebel, M. A., Hampson, P., Gueyrard, D., Pelotier, B., Yli-Kauhaluoma, J., Piva, O., Lord, J. M., & Goekjian, P. G. (2012). Total synthesis of bistramide A and its 36(Z) isomers: differential effect on cell division, differentiation, and apoptosis. Chemistry: A European Journal, 18(24), 7452-66. https://doi.org/10.1002/chem.201102462

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abstract = "The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product.",

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T2 - differential effect on cell division, differentiation, and apoptosis

AU - Tomas, Loïc

AU - Boije af Gennäs, Gustav

AU - Hiebel, Marie Aude

AU - Hampson, Peter

AU - Gueyrard, David

AU - Pelotier, Béatrice

AU - Yli-Kauhaluoma, Jari

AU - Piva, Olivier

AU - Lord, Janet M

AU - Goekjian, Peter G

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AB - The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product.

KW - Acetamides

KW - Apoptosis

KW - Cell Division

KW - Cyclization

KW - HL-60 Cells

KW - Humans

KW - Molecular Structure

KW - Pyrans

KW - Spiro Compounds

KW - Stereoisomerism

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DO - 10.1002/chem.201102462

M3 - Article

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JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

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