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

8 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 - 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.\}",

year = "2003",

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

language = "English (US)",

pages = "647--650",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "5",

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TY - JOUR

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

Y1 - 2003

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

UR - https://www.scopus.com/pages/publications/0037266959

UR - https://www.scopus.com/inward/citedby.url?scp=0037266959&partnerID=8YFLogxK

U2 - 10.1055/s-2003-38368

DO - 10.1055/s-2003-38368

M3 - Article

AN - SCOPUS:0037266959

SN - 0936-5214

SP - 647

EP - 650

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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