Acylation of novobiocin by carboxylic acid anhydrides: Preparation and characterization of semi-synthetic novenamines

Yifat Berkov-Zrihen; Roi Rutenberg; Micha Fridman

doi:10.1016/j.tet.2012.01.042

Acylation of novobiocin by carboxylic acid anhydrides: Preparation and characterization of semi-synthetic novenamines

Yifat Berkov-Zrihen, Roi Rutenberg, Micha Fridman

School of Chemistry

Tel Aviv University

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

Abstract

The acylation of novobiocin by carboxylic acid anhydrides leading to preparation of three families of semi-synthetic acylated novenamine analogues is reported. ESI-MS was used to monitor the reaction progress and enabled the isolation of intermediate compounds that provided insights into the sequence of acylation steps during the reaction. The chemoselectivity of the reaction depends on the carboxylic acid anhydride. The potential of the acylated novenamine analogues as leads for the development of antibacterial agents is discussed.

Original language	English
Pages (from-to)	2306-2312
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2012.01.042
State	Published - 11 Mar 2012

Keywords

Aminocoumarins
Novenamine
Noviose
Novobiocin
Semi-synthetic aminocoumarins

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.01.042

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title = "Acylation of novobiocin by carboxylic acid anhydrides: Preparation and characterization of semi-synthetic novenamines",

abstract = "The acylation of novobiocin by carboxylic acid anhydrides leading to preparation of three families of semi-synthetic acylated novenamine analogues is reported. ESI-MS was used to monitor the reaction progress and enabled the isolation of intermediate compounds that provided insights into the sequence of acylation steps during the reaction. The chemoselectivity of the reaction depends on the carboxylic acid anhydride. The potential of the acylated novenamine analogues as leads for the development of antibacterial agents is discussed.",

keywords = "Aminocoumarins, Novenamine, Noviose, Novobiocin, Semi-synthetic aminocoumarins",

author = "Yifat Berkov-Zrihen and Roi Rutenberg and Micha Fridman",

note = "Funding Information: We would like to thank the Tel Aviv University Start-up Fund for the financial support of this study. We would like to thank Prof. Shmuel Carmeli from the School of Chemistry at Tel Aviv University for his advice on compound characterization.",

year = "2012",

month = mar,

day = "11",

doi = "10.1016/j.tet.2012.01.042",

language = "الإنجليزيّة",

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T1 - Acylation of novobiocin by carboxylic acid anhydrides

T2 - Preparation and characterization of semi-synthetic novenamines

AU - Berkov-Zrihen, Yifat

AU - Rutenberg, Roi

AU - Fridman, Micha

N1 - Funding Information: We would like to thank the Tel Aviv University Start-up Fund for the financial support of this study. We would like to thank Prof. Shmuel Carmeli from the School of Chemistry at Tel Aviv University for his advice on compound characterization.

PY - 2012/3/11

Y1 - 2012/3/11

N2 - The acylation of novobiocin by carboxylic acid anhydrides leading to preparation of three families of semi-synthetic acylated novenamine analogues is reported. ESI-MS was used to monitor the reaction progress and enabled the isolation of intermediate compounds that provided insights into the sequence of acylation steps during the reaction. The chemoselectivity of the reaction depends on the carboxylic acid anhydride. The potential of the acylated novenamine analogues as leads for the development of antibacterial agents is discussed.

AB - The acylation of novobiocin by carboxylic acid anhydrides leading to preparation of three families of semi-synthetic acylated novenamine analogues is reported. ESI-MS was used to monitor the reaction progress and enabled the isolation of intermediate compounds that provided insights into the sequence of acylation steps during the reaction. The chemoselectivity of the reaction depends on the carboxylic acid anhydride. The potential of the acylated novenamine analogues as leads for the development of antibacterial agents is discussed.

KW - Aminocoumarins

KW - Novenamine

KW - Noviose

KW - Novobiocin

KW - Semi-synthetic aminocoumarins

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U2 - 10.1016/j.tet.2012.01.042

DO - 10.1016/j.tet.2012.01.042

M3 - مقالة

SN - 0040-4020

VL - 68

SP - 2306

EP - 2312

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Acylation of novobiocin by carboxylic acid anhydrides: Preparation and characterization of semi-synthetic novenamines

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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