Nucleotides. Part XLIII.  Solid‐phase synthesis of oligoribonucleotides using the 2‐dansylethoxycarbonyl (  2‐{[5‐(dimethylamino)naphthalen‐1‐yl]sulfonyl}ethoxycarbonyl; dnseoc) group for 5′‐hydroxy protection | Zendy

Bergmann Frank | Zendy; Pfleiderer Wolfgang | Zendy

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Nucleotides. Part XLIII. Solid‐phase synthesis of oligoribonucleotides using the 2‐dansylethoxycarbonyl (  2‐{[5‐(dimethylamino)naphthalen‐1‐yl]sulfonyl}ethoxycarbonyl; dnseoc) group for 5′‐hydroxy protection

Author(s) -

Bergmann Frank,

Pfleiderer Wolfgang

Publication year - 1994

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19940770411

Subject(s) - chemistry , sulfonyl , solid phase synthesis , nucleotide , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , peptide , alkyl , gene

A new efficient method for solid‐phase synthesis of oligoribonucleotides via the phosphoramidite approach is described. The combination of the base‐labile 2‐dansylethoxycarbonyl (Dnseoc) group for 5′‐OH protection with the acid‐labile tetrahydro‐4‐methoxy‐2 H ‐pyran‐4‐yl (Thmp) group as 2′‐OH blocking group is orthogonal regarding cleavage reactions and fulfills the requirements of an automated synthesis in an excellent manner if the phosphoramidite function carries the N,N ‐diethyl‐ O ‐[2‐(4‐nitrophenyl)ethyl] substitution.

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