A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues. / Wellendorph, Petrine; Jaroszewski, Jerzy W; Hansen, Steen Honoré; Franzyk, Henrik.

In: European Journal of Medicinal Chemistry, Vol. 38, No. 1, 2003, p. 117-22.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Wellendorph, P, Jaroszewski, JW, Hansen, SH & Franzyk, H 2003, 'A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues', European Journal of Medicinal Chemistry, vol. 38, no. 1, pp. 117-22.

APA

Wellendorph, P., Jaroszewski, J. W., Hansen, S. H., & Franzyk, H. (2003). A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues. European Journal of Medicinal Chemistry, 38(1), 117-22.

Vancouver

Wellendorph P, Jaroszewski JW, Hansen SH, Franzyk H. A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues. European Journal of Medicinal Chemistry. 2003;38(1):117-22.

Author

Wellendorph, Petrine ; Jaroszewski, Jerzy W ; Hansen, Steen Honoré ; Franzyk, Henrik. / A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues. In: European Journal of Medicinal Chemistry. 2003 ; Vol. 38, No. 1. pp. 117-22.

Bibtex

@article{b44c86b9461f4992b1ebeef13bad8e8a,
title = "A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues",
abstract = "A general, improved procedure for rapid synthesis of philanthotoxin analogues, a pharmacologically important class of polyamine conjugates, is described. The solution-phase procedure is illustrated by gram-scale synthesis of philanthotoxins PhTX-343 and PhTX-12. Selectively protected polyamines are coupled to N(alpha)-Fmoc-protected amino acid pentafluorophenyl esters. After removal of the N(alpha)-Fmoc group, the amine is coupled with carboxylic acid pentafluorophenyl esters. Deprotection followed by a rapid and efficient purification by vacuum liquid chromatography on octadecylsilyl silica (RP-18 phase) gave the philanthotoxin analogues in 74-78% overall yield.",
keywords = "Chromatography, Liquid, Combinatorial Chemistry Techniques, Electrophoresis, Capillary, Magnetic Resonance Spectroscopy, Models, Chemical, Phenols, Polyamines, Silica Gel, Silicon Dioxide, Solutions, Tyrosine",
author = "Petrine Wellendorph and Jaroszewski, {Jerzy W} and Hansen, {Steen Honor{\'e}} and Henrik Franzyk",
note = "Copyright 2002 Editions scienctifiques et m{\'e}dicales Elsevier SAS",
year = "2003",
language = "English",
volume = "38",
pages = "117--22",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier Masson",
number = "1",

}

RIS

TY - JOUR

T1 - A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues

AU - Wellendorph, Petrine

AU - Jaroszewski, Jerzy W

AU - Hansen, Steen Honoré

AU - Franzyk, Henrik

N1 - Copyright 2002 Editions scienctifiques et médicales Elsevier SAS

PY - 2003

Y1 - 2003

N2 - A general, improved procedure for rapid synthesis of philanthotoxin analogues, a pharmacologically important class of polyamine conjugates, is described. The solution-phase procedure is illustrated by gram-scale synthesis of philanthotoxins PhTX-343 and PhTX-12. Selectively protected polyamines are coupled to N(alpha)-Fmoc-protected amino acid pentafluorophenyl esters. After removal of the N(alpha)-Fmoc group, the amine is coupled with carboxylic acid pentafluorophenyl esters. Deprotection followed by a rapid and efficient purification by vacuum liquid chromatography on octadecylsilyl silica (RP-18 phase) gave the philanthotoxin analogues in 74-78% overall yield.

AB - A general, improved procedure for rapid synthesis of philanthotoxin analogues, a pharmacologically important class of polyamine conjugates, is described. The solution-phase procedure is illustrated by gram-scale synthesis of philanthotoxins PhTX-343 and PhTX-12. Selectively protected polyamines are coupled to N(alpha)-Fmoc-protected amino acid pentafluorophenyl esters. After removal of the N(alpha)-Fmoc group, the amine is coupled with carboxylic acid pentafluorophenyl esters. Deprotection followed by a rapid and efficient purification by vacuum liquid chromatography on octadecylsilyl silica (RP-18 phase) gave the philanthotoxin analogues in 74-78% overall yield.

KW - Chromatography, Liquid

KW - Combinatorial Chemistry Techniques

KW - Electrophoresis, Capillary

KW - Magnetic Resonance Spectroscopy

KW - Models, Chemical

KW - Phenols

KW - Polyamines

KW - Silica Gel

KW - Silicon Dioxide

KW - Solutions

KW - Tyrosine

M3 - Journal article

C2 - 12593922

VL - 38

SP - 117

EP - 122

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

IS - 1

ER -

ID: 42389845