Synthesis and structure-activity relationships of novel 3'-Hty- substituted pneumocandins

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

doi:10.1016/S0960-894X(97)10107-X

Synthesis and structure-activity relationships of novel 3'-Hty- substituted pneumocandins

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

Center for Discovery and Innovation

Merck

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

11 Scopus citations

Abstract

A series of pneumocandin B₀ analogs substituted at the 3'-position of the homotyrosine (Hty) residue have been prepared and evaluated for their inhibition of 1,3-β-(D)-glucan synthesis and for their antifungal activity against C. albicans. Cationic analogs displayed enhanced antifungal properties. The phenolic hydroxyl is involved in a critical hydrogen-bond at the binding site of the enzyme.

Original language	English
Pages (from-to)	2879-2884
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	7
Issue number	22
DOIs	https://doi.org/10.1016/S0960-894X(97)10107-X
State	Published - 18 Nov 1997

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title = "Synthesis and structure-activity relationships of novel 3'-Hty- substituted pneumocandins",

abstract = "A series of pneumocandin B0 analogs substituted at the 3'-position of the homotyrosine (Hty) residue have been prepared and evaluated for their inhibition of 1,3-β-(D)-glucan synthesis and for their antifungal activity against C. albicans. Cationic analogs displayed enhanced antifungal properties. The phenolic hydroxyl is involved in a critical hydrogen-bond at the binding site of the enzyme.",

author = "Black, \{Regina M.\} and Balkovec, \{James M.\} and Nollstadt, \{Karl M.\} and Sarah Dreikorn and Bartizal, \{Kenneth F.\} and Abruzzo, \{George K.\}",

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T1 - Synthesis and structure-activity relationships of novel 3'-Hty- substituted pneumocandins

AU - Black, Regina M.

AU - Balkovec, James M.

AU - Nollstadt, Karl M.

AU - Dreikorn, Sarah

AU - Bartizal, Kenneth F.

AU - Abruzzo, George K.

PY - 1997/11/18

Y1 - 1997/11/18

N2 - A series of pneumocandin B0 analogs substituted at the 3'-position of the homotyrosine (Hty) residue have been prepared and evaluated for their inhibition of 1,3-β-(D)-glucan synthesis and for their antifungal activity against C. albicans. Cationic analogs displayed enhanced antifungal properties. The phenolic hydroxyl is involved in a critical hydrogen-bond at the binding site of the enzyme.

AB - A series of pneumocandin B0 analogs substituted at the 3'-position of the homotyrosine (Hty) residue have been prepared and evaluated for their inhibition of 1,3-β-(D)-glucan synthesis and for their antifungal activity against C. albicans. Cationic analogs displayed enhanced antifungal properties. The phenolic hydroxyl is involved in a critical hydrogen-bond at the binding site of the enzyme.

UR - https://www.scopus.com/pages/publications/0030670334

U2 - 10.1016/S0960-894X(97)10107-X

DO - 10.1016/S0960-894X(97)10107-X

M3 - Article

AN - SCOPUS:0030670334

SN - 0960-894X

VL - 7

SP - 2879

EP - 2884

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 22

ER -

Synthesis and structure-activity relationships of novel 3'-Hty- substituted pneumocandins

Abstract

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