Expeditious synthesis of 'P'-protected macrocycles en route to lanthanide chelate metal complexes

H. Charles Manning; Mingfeng Bai; Bernard M. Anderson; Rafal Lisiak; Lynn E. Samuelson; Darryl J. Bornhop

doi:10.1016/j.tetlet.2005.05.049

Expeditious synthesis of 'P'-protected macrocycles en route to lanthanide chelate metal complexes

H. Charles Manning, Mingfeng Bai, Bernard M. Anderson, Rafal Lisiak, Lynn E. Samuelson, Darryl J. Bornhop

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

14 Scopus citations

Abstract

Phosphonic acid appended tetraazacyclododecane (cyclen)-based macrocycles are attractive metal-ion chelators for diagnostic imaging and therapeutic delivery. Here, we report a novel P-protected methodology that facilitates the rapid synthesis and purification of targeted phosphonic acid bearing macrocycles. Purification of these intermediates is facile, and deprotection using neat TFA is rapid, yet mild enough to preserve the integrity of delicate peptides and/or targeting moieties.

Original language	English (US)
Pages (from-to)	4707-4710
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	28
DOIs	https://doi.org/10.1016/j.tetlet.2005.05.049
State	Published - Jul 11 2005
Externally published	Yes

Keywords

Lanthanide chelate
MRI
Phosphonate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.05.049

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title = "Expeditious synthesis of 'P'-protected macrocycles en route to lanthanide chelate metal complexes",

abstract = "Phosphonic acid appended tetraazacyclododecane (cyclen)-based macrocycles are attractive metal-ion chelators for diagnostic imaging and therapeutic delivery. Here, we report a novel P-protected methodology that facilitates the rapid synthesis and purification of targeted phosphonic acid bearing macrocycles. Purification of these intermediates is facile, and deprotection using neat TFA is rapid, yet mild enough to preserve the integrity of delicate peptides and/or targeting moieties.",

keywords = "Lanthanide chelate, MRI, Phosphonate",

author = "Manning, {H. Charles} and Mingfeng Bai and Anderson, {Bernard M.} and Rafal Lisiak and Samuelson, {Lynn E.} and Bornhop, {Darryl J.}",

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T1 - Expeditious synthesis of 'P'-protected macrocycles en route to lanthanide chelate metal complexes

AU - Manning, H. Charles

AU - Bai, Mingfeng

AU - Anderson, Bernard M.

AU - Lisiak, Rafal

AU - Samuelson, Lynn E.

AU - Bornhop, Darryl J.

PY - 2005/7/11

Y1 - 2005/7/11

N2 - Phosphonic acid appended tetraazacyclododecane (cyclen)-based macrocycles are attractive metal-ion chelators for diagnostic imaging and therapeutic delivery. Here, we report a novel P-protected methodology that facilitates the rapid synthesis and purification of targeted phosphonic acid bearing macrocycles. Purification of these intermediates is facile, and deprotection using neat TFA is rapid, yet mild enough to preserve the integrity of delicate peptides and/or targeting moieties.

AB - Phosphonic acid appended tetraazacyclododecane (cyclen)-based macrocycles are attractive metal-ion chelators for diagnostic imaging and therapeutic delivery. Here, we report a novel P-protected methodology that facilitates the rapid synthesis and purification of targeted phosphonic acid bearing macrocycles. Purification of these intermediates is facile, and deprotection using neat TFA is rapid, yet mild enough to preserve the integrity of delicate peptides and/or targeting moieties.

KW - Lanthanide chelate

KW - MRI

KW - Phosphonate

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DO - 10.1016/j.tetlet.2005.05.049

M3 - Article

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SN - 0040-4039

VL - 46

SP - 4707

EP - 4710

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

Expeditious synthesis of 'P'-protected macrocycles en route to lanthanide chelate metal complexes

Abstract

Keywords

ASJC Scopus subject areas

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