Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra

Jorma Hassfeld; Christophe Farès; Heinrich Steinmetz; Teresa Carlomagno; Dirk Menche

doi:10.1021/ol061831y

Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra

Jorma Hassfeld
, Christophe Farès
, Heinrich Steinmetz
, Teresa Carlomagno
, Dirk Menche

Biosciences

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

Abstract

[structure: see text] The relative and absolute stereochemistry of the structurally unique 24-membered myxobacterial macrolides archazolid A and B, highly potent vacuolar-type ATPase (V-ATPase) inhibitors in vitro and in vivo, was determined on the basis of a combination of extensive high-field NMR studies, including J-based configuration analysis, molecular modeling, and chemical methods.

Original language	English
Pages (from-to)	4751-4
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	21
DOIs	https://doi.org/10.1021/ol061831y
Publication status	Published - 12 Oct 2006

Keywords

Antimitotic Agents/chemistry
Macrolides/chemistry
Molecular Structure
Myxococcales/chemistry
Stereoisomerism
Thiazoles/chemistry
Vacuolar Proton-Translocating ATPases/antagonists & inhibitors

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10.1021/ol061831y

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title = "Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra",

abstract = "[structure: see text] The relative and absolute stereochemistry of the structurally unique 24-membered myxobacterial macrolides archazolid A and B, highly potent vacuolar-type ATPase (V-ATPase) inhibitors in vitro and in vivo, was determined on the basis of a combination of extensive high-field NMR studies, including J-based configuration analysis, molecular modeling, and chemical methods.",

keywords = "Antimitotic Agents/chemistry, Macrolides/chemistry, Molecular Structure, Myxococcales/chemistry, Stereoisomerism, Thiazoles/chemistry, Vacuolar Proton-Translocating ATPases/antagonists \& inhibitors",

author = "Jorma Hassfeld and Christophe Far{\`e}s and Heinrich Steinmetz and Teresa Carlomagno and Dirk Menche",

year = "2006",

month = oct,

day = "12",

doi = "10.1021/ol061831y",

language = "English",

volume = "8",

pages = "4751--4",

journal = "Organic Letters",

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T1 - Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra

AU - Hassfeld, Jorma

AU - Farès, Christophe

AU - Steinmetz, Heinrich

AU - Carlomagno, Teresa

AU - Menche, Dirk

PY - 2006/10/12

Y1 - 2006/10/12

N2 - [structure: see text] The relative and absolute stereochemistry of the structurally unique 24-membered myxobacterial macrolides archazolid A and B, highly potent vacuolar-type ATPase (V-ATPase) inhibitors in vitro and in vivo, was determined on the basis of a combination of extensive high-field NMR studies, including J-based configuration analysis, molecular modeling, and chemical methods.

AB - [structure: see text] The relative and absolute stereochemistry of the structurally unique 24-membered myxobacterial macrolides archazolid A and B, highly potent vacuolar-type ATPase (V-ATPase) inhibitors in vitro and in vivo, was determined on the basis of a combination of extensive high-field NMR studies, including J-based configuration analysis, molecular modeling, and chemical methods.

KW - Antimitotic Agents/chemistry

KW - Macrolides/chemistry

KW - Molecular Structure

KW - Myxococcales/chemistry

KW - Stereoisomerism

KW - Thiazoles/chemistry

KW - Vacuolar Proton-Translocating ATPases/antagonists & inhibitors

U2 - 10.1021/ol061831y

DO - 10.1021/ol061831y

M3 - Article

C2 - 17020294

SN - 1523-7060

VL - 8

SP - 4751

EP - 4754

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra

Abstract

Keywords

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