Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity

Jane B. Laursen; Peter C. De Visser; Henrik K. Nielsen; Knud J. Jensen; John Nielsen

doi:10.1016/S0960-894X(01)00692-8

Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity

Jane B. Laursen, Peter C. De Visser, Henrik K. Nielsen, Knud J. Jensen, John Nielsen^*

^*Corresponding author for this work

20 Citations (Scopus)

Abstract

An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH₂Cl₂ (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.

Original language	English
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	12
Issue number	2
Pages (from-to)	171-175
Number of pages	5
ISSN	0960-894X
DOIs	https://doi.org/10.1016/S0960-894X(01)00692-8
Publication status	Published - 21 Jan 2002

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title = "Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity",

abstract = "An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.",

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T1 - Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity

AU - Laursen, Jane B.

AU - De Visser, Peter C.

AU - Nielsen, Henrik K.

AU - Jensen, Knud J.

AU - Nielsen, John

PY - 2002/1/21

Y1 - 2002/1/21

N2 - An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.

AB - An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.

U2 - 10.1016/S0960-894X(01)00692-8

DO - 10.1016/S0960-894X(01)00692-8

M3 - Journal article

C2 - 11755347

AN - SCOPUS:0037147788

SN - 0960-894X

VL - 12

SP - 171

EP - 175

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 2

ER -

Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity

Abstract

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