Total stepwise solid-phase synthesis of peptide-oligonucleotide conjugates using side-chain Boc/tBu protecting groups

A practical strategy for the total stepwise solid-phase synthesis of peptide-oligonucleotide conjugates was developed. In this strategy, the Boc/tBu protecting groups are utilized for the side chains of Trp, His, Arg, Asp, and Glu, and is deprotected in borate buffer at 90 degrees C to avoid depurin...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 59; no. 39; pp. 5839 - 5842
Main Authors Wang, Tao, Cao, Xiuxiu, Zheng, Yong, Chen, Chenchen, Zhou, Li, Sun, Demeng, Fang, Gemin, Tian, Changlin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 11.05.2023
Royal Society of Chemistry
Subjects
Amino acids
Chemistry
Chemistry, Multidisciplinary
Conjugates
Physical Sciences
Science & Technology
Solid phase synthesis
DELIVERY
Online AccessGet full text

Cover

More Information
Summary:A practical strategy for the total stepwise solid-phase synthesis of peptide-oligonucleotide conjugates was developed. In this strategy, the Boc/tBu protecting groups are utilized for the side chains of Trp, His, Arg, Asp, and Glu, and is deprotected in borate buffer at 90 degrees C to avoid depurination of the oligonucleotide caused by strong acid treatment. The advantage of this strategy is that the abovementioned amino acids are readily available in the market and the side reaction of deguanidination of the Arg residue can be avoided. This side-chain Boc/tBu protection strategy will expand the applicability of total stepwise synthesis in the preparation of peptide-oligonucleotide conjugates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00868a