155138-06-0Relevant academic research and scientific papers
Chemoenzymatic synthesis of nucleopeptides
Flohr, Stefanie,Jungmann, Volker,Waldmann, Herbert
, p. 669 - 681 (2007/10/03)
Nucleoproteins, in which the hydroxy group of a serine, a threonine, or a tyrosine, is linked through a phosphodiester group to the 3′- or 5′-end of DNA or RNA, play decisive roles in important biological processes. They may even have a major part in the process of viral replication by nucleoprotein-primed elongation of the oligonucleotide strand. For the study of the biological phenomena, in which nucleoproteins are involved, nucleopeptides with the characteristic linkage between the peptide chain and the oligonucleotide of their parent nucleoproteins may serve as powerful tools. However, the synthesis of these compounds is complicated by their pronounced acid- and base-lability, as well as their multifunctionality. As a result, protecting groups, which can be removed under the mildest conditions, are required. For the construction of such peptide conjugates using a flexible building block strategy, a combination of enzyme-labile and chemical protecting groups was developed. The C-terminal blocking function can be removed selectively from fully protected nucleoamino acid methyl, 2-methoxyethyl (ME), and methoxyethoxyethyl (MEE) esters by saponification of the esters. After elongation of the peptide chain with amino acid or peptide methyl, ME, MEE, and choline esters, the C-terminal ester blocking group can again be removed easily. The methyl, ME, and MEE esters are cleaved off with lipase, and the choline ester group is selectively attacked by butyrylcholine esterase. The nucleoamino acids and peptides formed may be fully deprotected. To this end, the enzyme-labile N-phenylacetyl (PhAc) group, which was employed to mask the amino functions of the nucleobases, was removed. The O-acetate in the deoxyribose was saponified, and the allyl protecting groups present were cleaved by Pd0-mediated allyl transfer. By combination of these techniques, a nucleopeptide was produced, which represents the characteristic linkage region of the nucleoprotein of adenovions 2. The conditions, under which the enzymatic deprotections proceed, are so mild that no undesired side reaction is observed, that is no depurination or β elimination of the nucleosides occurs. In addition, the specificity of the biocatalysts ensures that the peptide bonds and the other protecting groups present are not attacked either.
An enzymatic protecting group strategy for the synthesis of nucleopeptides
Jungmann, Volker,Waldmann, Herbert
, p. 1139 - 1142 (2007/10/03)
Enzymatic protecting group techniques are used for the selective synthesis of acid- and base labile multifunctional nucleopeptides under mild conditions.
Chemoenzymatic synthesis of nucleopeptides
Waldmann, Herbert,Gabold, Stefanie
, p. 1861 - 1862 (2007/10/03)
Acid- and base-labile multifunctional nucleopeptides have been selectively constructed under mild conditions by means of enzymatic protecting group techniques.
Chemoenzymic synthesis of P(α)-methyl deoxynucleoside triphosphates
Dineva, Magda A.,Petkov, Dimiter D.
, p. 1459 - 1467 (2007/10/03)
5'-O-(methylphosphonyl)-N-(phenylacetyl)-2'-deoxycytidine, deoxyadenosine and deoxyguanosine were pyrophosphorylated and the resulting N-protected P(α)-methyl nucleoside triphosphates were deblocked by treatment with penicillin amidase at pH 7.8, 25°C to give P(α)-methyl nucleoside triphosphates.
A simple method for N-acylation of adenosine and cytidine nucleosides using carboxylic acids activated in-situ with carbonyldiimidazole
Sinha,Sinha, Nanda D.,Davis,Davis, Peter,Schultze,Schultze, Lisa M.,Upadhya,Upadhya, Krishna
, p. 9277 - 9280 (2007/10/02)
Carboxylic acids are activated with 1,1'-carbonyldiimidazole in acetonitrile to form N-acylimidazoles which are then treated with per-trimethylsilyl ethers of nucleosides adenosine or cytidine at ambient temperature to generate exclusively N-acylated-Aden
