Pneumocandin antifungal lipopeptides. The phenolic hydroxyl is required for 1,3-β-glucan synthesis inhibition.

James M. Balkovec; Regina M. Black; George K. Abruzzo; Ken Bartizal; Sarah Dreikorn; Nollstadt Karl

doi:10.1016/S0960-894X(01)81010-6

Pneumocandin antifungal lipopeptides. The phenolic hydroxyl is required for 1,3-β-glucan synthesis inhibition.

James M. Balkovec
, Regina M. Black
, George K. Abruzzo
, Ken Bartizal
, Sarah Dreikorn
, Nollstadt Karl

Center for Discovery and Innovation

Merck

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

22 Scopus citations

Abstract

Pneumocandin B₀ 1 undergoes selective oxidation / reduction chemistry at the homotyrosine (hty) residue. Removal of the phenolic hydroxyl gives >140-fold loss in activity against a Candida albicans 1,3-β-glucan synthetase enzyme preparation and a significant loss of antifungal activity. Inversion of the C4-hty hydroxyl causes about a 70-fold decrease in potency, while removal of this hydroxyl yields a more potent inhibitor.

Original language	English
Pages (from-to)	2039-2042
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	3
Issue number	10
DOIs	https://doi.org/10.1016/S0960-894X(01)81010-6
State	Published - Oct 1993

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title = "Pneumocandin antifungal lipopeptides. The phenolic hydroxyl is required for 1,3-β-glucan synthesis inhibition.",

abstract = "Pneumocandin B0 1 undergoes selective oxidation / reduction chemistry at the homotyrosine (hty) residue. Removal of the phenolic hydroxyl gives >140-fold loss in activity against a Candida albicans 1,3-β-glucan synthetase enzyme preparation and a significant loss of antifungal activity. Inversion of the C4-hty hydroxyl causes about a 70-fold decrease in potency, while removal of this hydroxyl yields a more potent inhibitor.",

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AU - Balkovec, James M.

AU - Black, Regina M.

AU - Abruzzo, George K.

AU - Bartizal, Ken

AU - Dreikorn, Sarah

AU - Karl, Nollstadt

PY - 1993/10

Y1 - 1993/10

N2 - Pneumocandin B0 1 undergoes selective oxidation / reduction chemistry at the homotyrosine (hty) residue. Removal of the phenolic hydroxyl gives >140-fold loss in activity against a Candida albicans 1,3-β-glucan synthetase enzyme preparation and a significant loss of antifungal activity. Inversion of the C4-hty hydroxyl causes about a 70-fold decrease in potency, while removal of this hydroxyl yields a more potent inhibitor.

AB - Pneumocandin B0 1 undergoes selective oxidation / reduction chemistry at the homotyrosine (hty) residue. Removal of the phenolic hydroxyl gives >140-fold loss in activity against a Candida albicans 1,3-β-glucan synthetase enzyme preparation and a significant loss of antifungal activity. Inversion of the C4-hty hydroxyl causes about a 70-fold decrease in potency, while removal of this hydroxyl yields a more potent inhibitor.

UR - https://www.scopus.com/pages/publications/0027440580

U2 - 10.1016/S0960-894X(01)81010-6

DO - 10.1016/S0960-894X(01)81010-6

M3 - Article

AN - SCOPUS:0027440580

SN - 0960-894X

VL - 3

SP - 2039

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

ER -

Pneumocandin antifungal lipopeptides. The phenolic hydroxyl is required for 1,3-β-glucan synthesis inhibition.

Abstract

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