Synthesis of leuprorelin using segment condensation approach

Tao Cen; Cheng Zhou; Xiuming Wu; Bo Jiang; Shemin Zhu; Shubao Shen

Synthesis of leuprorelin using segment condensation approach

Tao Cen, Cheng Zhou, Xiuming Wu, Bo Jiang, Shemin Zhu, Shubao Shen

College of Materials Science and Engineering

Nanjing Tech University

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

2 Scopus citations

Abstract

Leuprorelin was synthesized by segment condensation strategy (2+7). The protected dipeptide, Fmoc-Arg(Pbf)-Pro-NHEt, was synthesized in solution phase and its yield reached 84.8%, when DIC was used as the coupling reagent, THF as the solvent, and the molar ratio of Pro-NHEṫHCl and Fmoc-Arg(Pbf)-OH was 1 : 1.25. The protected pentapeptide synthesized in solid phase yielded 81.3%. The protected leuprorelin was synthesized by segment condensation using DMF : DMSO (V : V=1 : 1) as the solvent and HATU/HOBt/DIEA as the coupling reagent. The target product of leuprorelin was achieved after cutting the side-chain.

Original language	English
Pages (from-to)	837-842
Number of pages	6
Journal	Chinese Journal of Organic Chemistry
Volume	30
Issue number	6
State	Published - Jun 2010

Keywords

Difficult sequence
Leuprorelin
Peptide synthesis
Segment condensation

Cite this

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title = "Synthesis of leuprorelin using segment condensation approach",

abstract = "Leuprorelin was synthesized by segment condensation strategy (2+7). The protected dipeptide, Fmoc-Arg(Pbf)-Pro-NHEt, was synthesized in solution phase and its yield reached 84.8%, when DIC was used as the coupling reagent, THF as the solvent, and the molar ratio of Pro-NHEṫHCl and Fmoc-Arg(Pbf)-OH was 1 : 1.25. The protected pentapeptide synthesized in solid phase yielded 81.3%. The protected leuprorelin was synthesized by segment condensation using DMF : DMSO (V : V=1 : 1) as the solvent and HATU/HOBt/DIEA as the coupling reagent. The target product of leuprorelin was achieved after cutting the side-chain.",

keywords = "Difficult sequence, Leuprorelin, Peptide synthesis, Segment condensation",

author = "Tao Cen and Cheng Zhou and Xiuming Wu and Bo Jiang and Shemin Zhu and Shubao Shen",

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month = jun,

language = "英语",

volume = "30",

pages = "837--842",

journal = "Chinese Journal of Organic Chemistry",

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TY - JOUR

T1 - Synthesis of leuprorelin using segment condensation approach

AU - Cen, Tao

AU - Zhou, Cheng

AU - Wu, Xiuming

AU - Jiang, Bo

AU - Zhu, Shemin

AU - Shen, Shubao

PY - 2010/6

Y1 - 2010/6

N2 - Leuprorelin was synthesized by segment condensation strategy (2+7). The protected dipeptide, Fmoc-Arg(Pbf)-Pro-NHEt, was synthesized in solution phase and its yield reached 84.8%, when DIC was used as the coupling reagent, THF as the solvent, and the molar ratio of Pro-NHEṫHCl and Fmoc-Arg(Pbf)-OH was 1 : 1.25. The protected pentapeptide synthesized in solid phase yielded 81.3%. The protected leuprorelin was synthesized by segment condensation using DMF : DMSO (V : V=1 : 1) as the solvent and HATU/HOBt/DIEA as the coupling reagent. The target product of leuprorelin was achieved after cutting the side-chain.

AB - Leuprorelin was synthesized by segment condensation strategy (2+7). The protected dipeptide, Fmoc-Arg(Pbf)-Pro-NHEt, was synthesized in solution phase and its yield reached 84.8%, when DIC was used as the coupling reagent, THF as the solvent, and the molar ratio of Pro-NHEṫHCl and Fmoc-Arg(Pbf)-OH was 1 : 1.25. The protected pentapeptide synthesized in solid phase yielded 81.3%. The protected leuprorelin was synthesized by segment condensation using DMF : DMSO (V : V=1 : 1) as the solvent and HATU/HOBt/DIEA as the coupling reagent. The target product of leuprorelin was achieved after cutting the side-chain.

KW - Difficult sequence

KW - Leuprorelin

KW - Peptide synthesis

KW - Segment condensation

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M3 - 文章

AN - SCOPUS:77956592170

SN - 0253-2786

VL - 30

SP - 837

EP - 842

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

IS - 6

ER -

Synthesis of leuprorelin using segment condensation approach

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