Phosphoramidite derivatives, their preparation and the use thereof in the incorporation of reporter groups on synthetic oligonucleotides
First Claim
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1. A phosphoramidite derivative of the following formula:
- ##STR15## wherein X=biotin, andY=a protecting group.
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Abstract
Phosphoramidite derivatives of formula (V), ##STR1## wherein X is biotin and Y is a protecting group. There may be a linker arm, of variable length, between X and the rest of the molecule. Examples of the protecting group Y include 4,4'"'"'-dimethoxytrityl, trifluoroacetyl and fluorenylmethoxycarbonyl (Fmoc). The phosphoramidite derivatives are useful in single or multiple labelling of synthetic oligonucleotides. Process for the preparation of these phosphoramidite derivatives are also disclosed.
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6 Claims
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1. A phosphoramidite derivative of the following formula:
- ##STR15## wherein X=biotin, and
Y=a protecting group. - View Dependent Claims (2, 3, 5, 6)
- ##STR15## wherein X=biotin, and
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4. A method for the production of a phosphoramidite derivative of the following formula:
- ##STR16## and which comprises;
i) Reaction of solketal with acrylonitrile to form the addition product, 2-cyanoethyl solketal (I);
##STR17## ii) Reduction of the resultant compound (I) to form 3-aminopropyl solketal (II);
##STR18## iii) Reaction of the resultant compound (II) with biotin N-hydroxysuccinimide to form N-biotinyl-3-aminopropyl solketal (III);
##STR19## iv) Reaction of the resultant compound (III) with 4,4'"'"'-dimethoxytrityl chloride to form 1-0-(4, 4'"'"'-dimethoxytrityl)-3-0-(N-biotinyl-3-aminopropyl) glycerol (IV);
##STR20## v) Phosphitylation of the resultant compound (IV) to produce the desired biotinyl phosphoramidite derivative (V);
##STR21## wherein DMTr=4,4'"'"'-dimethoxytrityl.
- ##STR16## and which comprises;
Specification