Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

Evgeny A. Fadeev; Minkui Luo; John Taylor Groves

doi:10.1016/j.bmcl.2005.05.114

Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

Evgeny A. Fadeev, Minkui Luo, John Taylor Groves

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7 Scopus citations

Abstract

We describe two convenient syntheses of rhizobactin-1021 (Rz), a citrate-based siderophore amphiphile produced by the nitrogen-fixing root symbiont Rhizobium meliloti-1021, and several analogs. Our approach features a singly amidated, tert-butyl-protected citrate intermediate that easily affords a variety of Rz analogs in the late stages of the synthesis. Structural modeling and the monolayer behavior of Rz and its metal complexes are consistent with a structural reorganization upon Rz-mediated iron chelation.

Original language	English (US)
Pages (from-to)	3771-3774
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	16
DOIs	https://doi.org/10.1016/j.bmcl.2005.05.114
State	Published - Aug 15 2005

All Science Journal Classification (ASJC) codes

Drug Discovery
Molecular Medicine
Molecular Biology
Biochemistry
Clinical Biochemistry
Pharmaceutical Science
Organic Chemistry

Keywords

Acinetoferrin
Amphiphile
Iron
Mycobactin
Structure

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10.1016/j.bmcl.2005.05.114

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title = "Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs",

abstract = "We describe two convenient syntheses of rhizobactin-1021 (Rz), a citrate-based siderophore amphiphile produced by the nitrogen-fixing root symbiont Rhizobium meliloti-1021, and several analogs. Our approach features a singly amidated, tert-butyl-protected citrate intermediate that easily affords a variety of Rz analogs in the late stages of the synthesis. Structural modeling and the monolayer behavior of Rz and its metal complexes are consistent with a structural reorganization upon Rz-mediated iron chelation.",

keywords = "Acinetoferrin, Amphiphile, Iron, Mycobactin, Structure",

author = "Fadeev, \{Evgeny A.\} and Minkui Luo and Groves, \{John Taylor\}",

note = "Funding Information: Support of this work by the National Science Foundation (CHE-0316301 and CHE-0221978) through the Environmental Molecular Science Institute (CEBIC) at Princeton University is gratefully acknowledged. ",

year = "2005",

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doi = "10.1016/j.bmcl.2005.05.114",

language = "English (US)",

volume = "15",

pages = "3771--3774",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

AU - Fadeev, Evgeny A.

AU - Luo, Minkui

AU - Groves, John Taylor

N1 - Funding Information: Support of this work by the National Science Foundation (CHE-0316301 and CHE-0221978) through the Environmental Molecular Science Institute (CEBIC) at Princeton University is gratefully acknowledged.

PY - 2005/8/15

Y1 - 2005/8/15

N2 - We describe two convenient syntheses of rhizobactin-1021 (Rz), a citrate-based siderophore amphiphile produced by the nitrogen-fixing root symbiont Rhizobium meliloti-1021, and several analogs. Our approach features a singly amidated, tert-butyl-protected citrate intermediate that easily affords a variety of Rz analogs in the late stages of the synthesis. Structural modeling and the monolayer behavior of Rz and its metal complexes are consistent with a structural reorganization upon Rz-mediated iron chelation.

AB - We describe two convenient syntheses of rhizobactin-1021 (Rz), a citrate-based siderophore amphiphile produced by the nitrogen-fixing root symbiont Rhizobium meliloti-1021, and several analogs. Our approach features a singly amidated, tert-butyl-protected citrate intermediate that easily affords a variety of Rz analogs in the late stages of the synthesis. Structural modeling and the monolayer behavior of Rz and its metal complexes are consistent with a structural reorganization upon Rz-mediated iron chelation.

KW - Acinetoferrin

KW - Amphiphile

KW - Iron

KW - Mycobactin

KW - Structure

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DO - 10.1016/j.bmcl.2005.05.114

M3 - Article

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AN - SCOPUS:22844433791

SN - 0960-894X

VL - 15

SP - 3771

EP - 3774

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 16

ER -

Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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