Synthesis of pacidamycin analogues via an Ugi-multicomponent reaction

The second-generation synthesis of 3′-hydroxypacidamycin D (2) has been accomplished via an Ugi-four component reaction at a late stage of the synthesis. This approach provided ready access to a range of analogues including diastereomers of the diaminobutylic acid residue and hybrid-type analogues o...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-07, Vol.22 (14), p.4810-4815
Main Authors: Okamoto, Kazuya, Sakagami, Masahiro, Feng, Fei, Takahashi, Fumiyo, Uotani, Kouichi, Togame, Hiroko, Takemoto, Hiroshi, Ichikawa, Satoshi, Matsuda, Akira
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Antibacterial
Antibacterial agents
antibacterial properties
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
diastereomers
Hydroxylation
Medical sciences
Molecular Structure
Natural product
Nucleoside
Oligopeptides - chemical synthesis
Oligopeptides - pharmacology
Pharmacology. Drug treatments
Pseudomonas - drug effects
Pyrimidine Nucleosides - chemical synthesis
Pyrimidine Nucleosides - pharmacology
stereochemistry
Structure-Activity Relationship
Ugi-four component reaction
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Summary:The second-generation synthesis of 3′-hydroxypacidamycin D (2) has been accomplished via an Ugi-four component reaction at a late stage of the synthesis. This approach provided ready access to a range of analogues including diastereomers of the diaminobutylic acid residue and hybrid-type analogues of mureidomycins. Biological evaluations of these analogues indicated that the stereochemistry at the diaminobutylic acid residue has a crucial impact on both the MraY biochemical inhibition and whole-cell antibacterial activity.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.05.050