33485-36-8Relevant articles and documents
Compositions and Methods for Reverse Automated Nucleic Acid Synthesis
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Paragraph 0106-0107, (2019/10/29)
Methods for reverse automated nucleic acid synthesis, and 5′-H-phosphonates suitable for use in the same, as well as methods for making 5′-H-phosphonates, are described.
PARTIAL PROTECTION OF CARBOHYDRATE DERIVATIVES. PART 18. SIMPLE, PREPARATIVE PROCEDURE FOR 5'-O-ACYLRIBONUCLEOSIDES; HIGHLY REGIOSELECTIVE O-DEACyLATION AT 2' AND 3' POSITIONS OF FULLY ACYLATED PURINE AND PYRIMIDINE RIBONUCLEOSIDE THROUGH SODIUM METHOXYDE-THF SYSTEM
Nishino, Shigeyoshi,Rahman, MD. Azizur,Takamura, Hatsuko,Ishido, Yoshiharu
, p. 5503 - 5506 (2007/10/02)
A treatment of fully acylated purine and pyrimidine ribonucleosides with a small excess amount of sodium methoxide in THF at room temperature gave the corresponding 5'-acylates in excellent yields; N-acyl groups on the nucleic acid base moieties of adenosine and cytidine in addition to guanosine derivatives satisfactorily survived under the conditions used.
Synthesis of 2'(3')-O-Aminoacyl Triribonucleoside Diphosphates Using the Triester Method
Kumar, Gyanendra,Celewicz, Lech,Chladek, Stanislav
, p. 634 - 644 (2007/10/02)
Specific syntheses of 2'(3')-O-aminoacyl triribonucleoside diphosphates, C-C-A-Phe (16e), C-C-A-Ala (16f), and C-C-A-Gly (16g), which are the terminal sequences of corresponding aa-tRNAs and potential substrates for ribosomal peptidyltransferase, are described.The compounds 16e-g were synthesized by employing phosphotriester methods with a benzoyl group for protection of heterocyclic amino groups, a 2-chlorophenyl group for internucleotide phosphate protection, a monomethoxytrityl group for blocking of the 5'-hydroxy function, a 4-methoxytetrahydropyranyl group forprotection of 2'-hydroxy functions, and an N-benzyloxycarbonyl group for blocking of the α-amino acid.Protected dinucleotide block C-Cp (11b) was synthesized via the triester method and was condensed by using mesitylenesulfonyl tetrazolide with nucleoside components 9b and 10b, which have aminoacyl residues incorporated in the molecule, to yield protected aminoacyl trinucleotides 13a and 14 in 60-70percent yields.The fully protected aminoacyl trinucleotides 13a and 13b were also obtained from the protected C-C-A derivative 12 (with a free 3'-OH group on the 3'-terminus) by the aminoacylation reaction with corresponding N-benzyloxycarbonyl amino acids and mesitylenesulfonyl tetrazolide in 50-70percent yields.The protected derivatives 13a,b and 14 were deblocked to form C-C-A(Z-Phe) (16b), C-C-A(Z-Ala) (16c), and C-C-A(Z-Gly) (16d) in 15-40percent yields by reactions with N2H4, F-, and H+ (for 16b,c) or NH4OH and H+ (for 16d).The final products 16e-g were prepared by hydrogenolysis (Pd/BaSO4) of 16b-d in practically quantitative yields.The syntheses of all components (3a,c,4,9a,b, and 10b) for the triester approach to aminoacyl trinucleotides are also described.