3768-14-7

Usage

Uses

Used in Biomedical Research:
ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE is used as a research tool for studying its effects on adenosinergic signaling regulation via CD73 or ecto-5'-nucleotidase. It serves as an inhibitor of cluster of differentiation 73 (CD73), which is an enzyme involved in the conversion of adenosine monophosphate (AMP) to adenosine, a crucial signaling molecule with various physiological effects.
Used in Cell Culture Applications:
In the field of cell culture, ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE is used as a component of culture media. Its inclusion in the media allows researchers to investigate the role of CD73 and adenosinergic signaling in cellular processes, such as cell proliferation, differentiation, and migration. This helps in understanding the underlying mechanisms and potential therapeutic targets for various diseases and conditions.
Used in Drug Development:
The unique properties of ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE make it a promising candidate for drug development. Its ability to modulate adenosinergic signaling and inhibit CD73 activity can be harnessed to develop novel therapeutic agents targeting various diseases, including cancer, inflammatory disorders, and neurodegenerative diseases. Further research and development are needed to explore its potential applications and optimize its therapeutic efficacy.

Upstream product

• 58337-46-5 α,β-methylene-ATP lithium salt 
• 93978-76-8 tris(tetrabutylammonium) salt of methylenebis(phosphonic acid) 
• 5135-30-8 5'-tosyladenosine 

Downstream Products

• 102977-57-1 adenosine 5'- 5'<*>5'-ester with 2-β-D-ribofuranosyl-4-thiazolecarboxamide 

Relevant academic research and scientific papers

CONVENIENT SYNTHESES OF ADENOSINE 5'-DIPHOSPHATE, ADENOSINE 5'-METHYLENEDIPHOSPHONATE, AND ADENOSINE 5'-TRIPHOSPHATE

Adenosine 5'-tosylate is converted to adenosine 5'-diphosphate (ADP), adenosine 5'-methylenediphosphonate, and adenosine 5'-triphosphate (ATP) in good yields by direct displacement with the appropriate inorganic salt.

Combined Phosphoramidite-Phosphodiester Reagents for the Synthesis of Methylene Bisphosphonates

A new class of phosphanylmethylphosphonate reagents has been developed to enable the controlled synthesis of methylene bisphosphonate mono- and diesters. Condensation of such reagents with an alcohol of choice through azole-mediated phosphoramidite chemistry followed by in situ oxidation provides orthogonally protected methylene bisphosphonate tetraesters. Global deprotection of the tetraester leads to terminal methylene bisphosphonates. Alternatively, selective deprotection at the terminal phosphonate followed by a condensation between the acquired methylene bisphosphonate triester and a second alcohol leads to methylene bisphosphonates diesters.

2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate): A Versatile Reagent for the Synthesis of Nucleoside 5′-Methylenebis(phosphonate)s

2-(4-Nitrophenyl)ethyl methylenebis(phosphonate) (6) was prepared by reaction of equimolar amounts of 2-(4-nitrophenyl)ethyl alcohol and methylenebis(phosphonyl) tetrachloride in the presence of tetrazole. Compound 6 was further converted into the corresponding 4-nitrophenylethyl trisanhydride intermediate 7 by dehydration with diisopropylcarbodiimide (DIC). Reaction of 7 with either 2′,3′-O-isopropylideneadenosine (8a) or 2′,3′-O-isopropylideneguanosine (8b) afforded, after hydrolysis, the desired P 1-[2-(4-nitrophenyl)ethyl]-F2-(2′,3′-O- isopropylideneadenosin-5′-yl) methylenebis(phosphonate) (9a) and guanosine analogue 9b, respectively. A similar treatment of intermediate 7 with 3′-O-acetylthymidine (12a), 3′-O-acetyl-2′-deoxy-N4-benzoylcytidine (12b), 3′O-acetyl-2′-deoxy-N6-benzoyladenosine (12c), and 3′-O-acetyl-2′-deoxy-N2-isobutyrylguanosine (12d) gave the corresponding 2-(4-nitrophenyl)ethyl methylenebis(phosphonate)s 13a-d. These compounds as well as 9a,b were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) which caused elimination of the 2-(4-nitrophenyl)ethyl group. The base labile 3′-O-acetyl, N4-acetyl, N6-benzoyl, and N2-isobutyryl groups of 12a-d were also removed during the DBU treatment. Thus, the 5′methylenebis(phosphonate)s of 2′,3′-O-isopropylideneadenosine (10a), 2′,3′-O-isopropylideneguanosine (10b), thymidine (14a), 2′-deoxycytidine (14b), 2′-deoxyadenosine (14c), and 2′deoxyguanosine (14d) were prepared in good yield. De-O-isopropylidenation of 10a and 10b afforded adenosine 5′-methylenebis(phosphonate) (11a) and guanosine 5′-methylenebis(phosphonate) (11b), respectively.

Synthesis of Nucleotide 5'-Diphosphates from 5'-O-Tosyl Nucleosides

Procedures are described for the synthesis of nucleoside 5'-diphosphates, methanediphosphonates, and difluoromethanediphosphonates.The general strategy involves protection of the nucleosides as amidine, 2',3'-methoxymethylidene, and 3'-(tert-butyldimethylsilyl) derivatives prior to tosylation with tosyl chloride and (N,N-dimethylamino)pyridine.Deprotection, followed by displacement of the tosyl moiety with the tris(tetra-n-butylammonium) pyrophosphate, methanediphosphonate, or difluoromethanediphosphonate salts gave the desired products.The ammonium salts of the nucleotides were purified by flash chromatography on cellulose or medium pressure ion-exchange chromatography on DEAE Fractogel.Syntheses are reported for UDP (18), CDP (19), TDP (20), GDP (21), ADP (23), 2',3'-isopropylidene-ADP (22), adenosine 5'-methanediphosphonate (24), adenosine 5'-difluoromethanediphosphonate (25), and deoxyadenosine 5'-methanediphosphonate (27).In addition ATP (26) was prepared by treatment of 5'-O-tosyladenosine with tetrakis(tetra-n-butylammonium) thiophosphate.Yields for the displacement reactions ranged from 43percent to 93percent.

EVIDENCE A FOR PROTOPHOSPHATASE CATALYSED CLEAVAGE OF ADENOSINE TRIPHOSPHATE BY A DISSOCIATIVE-TYPE MECHANISM WITHIN A RECEPTOR-SUBSTRATE COMPLEX

Analogues of ATP and diadenosine 5',5''-P1,P4-tetraphosphate, Ap4A, have been used to explore the specificity and mechanism of the proto-ATPase activity of the macrocyclic polyamine -N6O2 (1).The results show that (1) has exonuclease-like activity and support a mechanism that is dissociative in character within a pre-associative scheme resulting from receptor-substrate binding.