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Chinese Journal of Organic Chemistry >

0 202503021 - 202503021

DOI: https://doi.org/10.6023/cjoc202503021

ARTICLE

Liquid-Phase Synthesis of Peptide Alcohol Assisted by a Hydrophobic Silica-Based Tag

  • Cheng Rong ,
  • Qian Yiyi ,
  • Xu Yuanqiang ,
  • Su Xianbin
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  • NanJing Tech University,Nan Jing,210000

Received date: 2025-04-17

  Revised date: 2025-05-04

  Online published: 2025-06-19

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Abstract

This study presents the development of a novel hydrophobic silicon-based tag, CBTBS [((chloromethylene)bis(1,4-phenylene))bis(oxy))bis(tert-butyldimethylsilane)], for facilitating the liquid-phase synthesis of peptide alcohols. By replacing the reproductive-toxic solvent N,N-dimethylformamide (DMF) with the environmentally friendly ethyl acetate (EA) and implementing a synergistic deprotection system using sodium 3-mercapto-1-propanesulfonate (Mps) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (substituting the traditionally regulated piperidine reagent), this strategy enables efficient and convenient removal of byproducts such as fulvene adducts. Additionally, it achieves high-efficiency synthesis of the Gramicidin A fragment with a crude yield exceeding 80%. Compared with conventional solid-phase synthesis, this method significantly reduces the process mass intensity (PMI), thereby providing an efficient and sustainable new pathway for the green synthesis of peptide alcohols.

Key words： hydrophobic silica-based tag; peptide alcohol; liquid phase synthesis; green

Cite this article

Cheng Rong , Qian Yiyi , Xu Yuanqiang , Su Xianbin . Liquid-Phase Synthesis of Peptide Alcohol Assisted by a Hydrophobic Silica-Based Tag[J]. Chinese Journal of Organic Chemistry, 0 : 202503021 -202503021 . DOI: 10.6023/cjoc202503021

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