3768-14-7

Basic information

• Product Name: ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE
• Synonyms: ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE;AMP-CP;ADENOSINE 5'-[ALPHA,BETA-METHYLENE]DIPHOSPHORIC ACID;ADP[ALPHA,BETA-CH2];adenosine5’-methylenediphosphate;adenosine 5'-[hydrogen (phosphonomethyl)phosphonate];A,B-METHYLENEADENOSINE 5'-DIPHOSPHATE*FR EE ACID;Adenosine5'-(alpha,beta-methylene)diphosphate
• CAS NO: 3768-14-7
• Molecular Formula: C₁₁H₁₇N₅O₉P₂
• Molecular Weight: 425.23
• EINECS: 223-194-0
• Mol File: 3768-14-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 895.6°Cat760mmHg
• Flash Point: 495.4°C
• Appearance: /
• Density: 2.35g/cm³
• Storage Temp.: −20°C
• PKA: 1.62±0.10(Predicted)
• BRN: 633678
• CAS DataBase Reference: ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE(3768-14-7)
• EPA Substance Registry System: ALPHA,BETA-METHYLENEADENOSINE 5'-DIPHOSPHATE(3768-14-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 3768-14-7(Hazardous Substances Data)

Usage

Uses

Adenosine 5′-(α,β-methylene)diphosphate has been used as a component of culture media, to study its effects as an inhibitor of cluster of differentiation 73 (CD73) and adenosinergic signaling regulation via CD73 or ecto-5′-nucleotidase.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.