Cleavage of oligodeoxyribonucleotides from controlled-pore glass supports and their rapid deprotection by gaseous amines.
A novel method for the deprotection of oligodeoxyribonucleotides has been developed. Gaseous amines such as ammonia or methylamine were employed under pressure to achieve mild and rapid deprotection conditions. For example, oligodeoxyribonucleotides having a (tert-butyl)phenoxyacetyl group for the protection of the exocyclic amino function of cytosine, adenine and guanine were released from controlled-pore glass supports and fully deprotected by ammonia or methylamine under gas phase conditions, at room temperature, within 35 or 2 min respectively.
Boal
J H
JH
Division of Hematologic Product, Center for Biologics Evaluation and Research, Food and Drug Administration, Bethesda, MD 20892, USA.
Wilk
A
A
Harindranath
N
N
Max
E E
EE
Kempe
T
T
Beaucage
S L
SL
D000225:Adenine / Q000031:analogs & derivatives; D000641:Ammonia / Q000737:chemistry; D001483:Base Sequence; D003596:Cytosine / Q000031:analogs & derivatives; D005740:Gases / Q000737:chemistry; D005898:Glass / Q000737:chemistry; D006147:Guanine / Q000031:analogs & derivatives; D008744:Methylamines / Q000737:chemistry; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry; D011312:Pressure
D005740:Gases; D008744:Methylamines; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D006147:Guanine; D000641:Ammonia; D003596:Cytosine; C027451:methylamine; D000225:Adenine