The tert.-Butyloxycarbonyl-(Boc) Group, a Suitable 2?-OH-Protecting Group in Oligoribonucleotide Solid-Phase Synthesis

1994 ◽  
Vol 336 (3) ◽  
pp. 233-236 ◽  
Author(s):  
G�nter Losse ◽  
Wolfgang Naumann ◽  
Andrea Winkler ◽  
Gabriele S�ptitz
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Group ◽  
Phase Synthesis ◽  
Group A

Solid-phase synthesis of 4-aminopiperidine analogues using the Alloc protecting group: an investigation of Alloc removal from secondary amines

2001 ◽  
Vol 42 (27) ◽  
pp. 4471-4474 ◽  
Author(s):  
Dolors Fernández-Forner ◽  
Gaspar Casals ◽  
Eloı́sa Navarro ◽  
Hamish Ryder ◽  
Fernando Albericio
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Secondary Amines ◽  
Protecting Group ◽  
Phase Synthesis

(2-Acetoxyphenoxy)ethyl (APOE) as a Phosphate Protecting Group in Solid-Phase Synthesis of Oligonucleotides via the Phosphoramidite Approach

2006 ◽  
Vol 10 (2) ◽  
pp. 251-256 ◽  
Author(s):  
Zacharia S. Cheruvallath ◽  
Alessandra Eleuteri ◽  
Brett Turney ◽  
Vasulinga T. Ravikumar
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Group ◽  
Phase Synthesis

scholarly journals Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

2019 ◽  
Vol 15 ◽  
pp. 1116-1128 ◽  
Author(s):  
Shahien Shahsavari ◽  
Dhananjani N A M Eriyagama ◽  
Bhaskar Halami ◽  
Vagarshak Begoyan ◽  
Marina Tanasova ◽  
...  
Keyword(s):  
Michael Addition ◽  
Steric Hindrance ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Side Product ◽  
Synthesis And Characterization ◽  
Protecting Group ◽  
Phase Synthesis ◽  
Improved Technology

Solid-phase synthesis of electrophilic oligodeoxynucleotides (ODNs) was achieved using dimethyl-Dmoc (dM-Dmoc) as amino protecting group. Due to the high steric hindrance of the 2-(propan-2-ylidene)-1,3-dithiane side product from deprotection, the use of excess nucleophilic scavengers such as aniline to prevent Michael addition of the side product to the deprotected ODN during ODN cleavage and deprotection was no longer needed. The improved technology was demonstrated by the synthesis and characterization of five ODNs including three modified ones. The modified ODNs contained the electrophilic groups ethyl ester, α-chloroamide, and thioester. Using the technology, the sensitive groups can be installed at any location within the ODN sequences without using any sequence- or functionality-specific conditions and procedures.

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