An efficient synthesis of a doxorubicin-peptide conjugate

Yao Jun Shi; Mark Cameron; Ulf H. Dolling; David R. Lieberman; Joseph E. Lynch; Robert A. Reamer; Michael A. Robbins; R. P. Volante; Paul J. Reider

doi:10.1055/s-2003-38368

An efficient synthesis of a doxorubicin-peptide conjugate

Yao Jun Shi, Mark Cameron, Ulf H. Dolling, David R. Lieberman, Joseph E. Lynch, Robert A. Reamer, Michael A. Robbins, R. P. Volante, Paul J. Reider

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

2 Scopus citations

Abstract

An efficient synthesis of the sodium salt of the doxorubicin-peptide conjugate 1, useful for the treatment of prostate cancer is described. The EDC-mediated amide formation between the heptapeptide 4 and doxorubicin (2) as the key step has been extensively studied employing peptide-coupling additives, such as 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) and 2-hydroxypyridine N-oxide (HOPO), surprisingly, mixing the additives HOAt and HOPO furnished the best results.

Original language	English (US)
Pages (from-to)	647-650
Number of pages	4
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-2003-38368
State	Published - Jan 1 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

Keywords

Amides
Coupling reaction
Isomerization
Peptide conjugate
Protecting group

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10.1055/s-2003-38368

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title = "An efficient synthesis of a doxorubicin-peptide conjugate",

abstract = "An efficient synthesis of the sodium salt of the doxorubicin-peptide conjugate 1, useful for the treatment of prostate cancer is described. The EDC-mediated amide formation between the heptapeptide 4 and doxorubicin (2) as the key step has been extensively studied employing peptide-coupling additives, such as 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) and 2-hydroxypyridine N-oxide (HOPO), surprisingly, mixing the additives HOAt and HOPO furnished the best results.",

keywords = "Amides, Coupling reaction, Isomerization, Peptide conjugate, Protecting group",

author = "Shi, {Yao Jun} and Mark Cameron and Dolling, {Ulf H.} and Lieberman, {David R.} and Lynch, {Joseph E.} and Reamer, {Robert A.} and Robbins, {Michael A.} and Volante, {R. P.} and Reider, {Paul J.}",

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doi = "10.1055/s-2003-38368",

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T1 - An efficient synthesis of a doxorubicin-peptide conjugate

AU - Shi, Yao Jun

AU - Cameron, Mark

AU - Dolling, Ulf H.

AU - Lieberman, David R.

AU - Lynch, Joseph E.

AU - Reamer, Robert A.

AU - Robbins, Michael A.

AU - Volante, R. P.

AU - Reider, Paul J.

PY - 2003/1/1

Y1 - 2003/1/1

N2 - An efficient synthesis of the sodium salt of the doxorubicin-peptide conjugate 1, useful for the treatment of prostate cancer is described. The EDC-mediated amide formation between the heptapeptide 4 and doxorubicin (2) as the key step has been extensively studied employing peptide-coupling additives, such as 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) and 2-hydroxypyridine N-oxide (HOPO), surprisingly, mixing the additives HOAt and HOPO furnished the best results.

AB - An efficient synthesis of the sodium salt of the doxorubicin-peptide conjugate 1, useful for the treatment of prostate cancer is described. The EDC-mediated amide formation between the heptapeptide 4 and doxorubicin (2) as the key step has been extensively studied employing peptide-coupling additives, such as 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) and 2-hydroxypyridine N-oxide (HOPO), surprisingly, mixing the additives HOAt and HOPO furnished the best results.

KW - Amides

KW - Coupling reaction

KW - Isomerization

KW - Peptide conjugate

KW - Protecting group

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DO - 10.1055/s-2003-38368

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JO - Synlett

JF - Synlett

IS - 5

ER -

An efficient synthesis of a doxorubicin-peptide conjugate

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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