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[ CAS No. 60-92-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 60-92-4
Chemical Structure| 60-92-4
Structure of 60-92-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 60-92-4 ]

CAS No. :60-92-4 MDL No. :
Formula : C10H12N5O6P Boiling Point : -
Linear Structure Formula :- InChI Key :IVOMOUWHDPKRLL-KQYNXXCUSA-N
M.W : 329.21 Pubchem ID :6076
Synonyms :
Cyclic adenosine monophosphate;Adenosine cyclic 3', 5'-monophosphate;NSC 143670;NSC 94017;Adenosine 3',5'-cyclic monophosphate;Adenosine Cyclophosphate;cAMP

Calculated chemistry of [ 60-92-4 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 9.0
Num. H-bond donors : 3.0
Molar Refractivity : 70.23
TPSA : 164.65 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.43
Log Po/w (XLOGP3) : -2.96
Log Po/w (WLOGP) : -1.13
Log Po/w (MLOGP) : -1.9
Log Po/w (SILICOS-IT) : -2.54
Consensus Log Po/w : -1.62

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : -0.25
Solubility : 184.0 mg/ml ; 0.558 mol/l
Class : Very soluble
Log S (Ali) : 0.06
Solubility : 380.0 mg/ml ; 1.16 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.49
Solubility : 1030.0 mg/ml ; 3.13 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.3

Safety of [ 60-92-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 60-92-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 60-92-4 ]

[ 60-92-4 ] Synthesis Path-Downstream   1~85

  • 4
  • [ 100-39-0 ]
  • C22H38N6O6P(1+) [ No CAS ]
  • [ 55053-32-2 ]
  • [ 137157-07-4 ]
  • [ 60-92-4 ]
  • [ 62742-71-6 ]
  • 5
  • [ 34051-17-7 ]
  • [ 60-92-4 ]
  • 6
  • [ 98-01-1 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-(6-[1-Furan-2-yl-meth-(Z)-ylidene]-amino}-purin-9-yl)-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 7
  • [ 624-76-0 ]
  • [ 60-92-4 ]
  • 6-Amino-9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1-(2-hydroxy-ethyl)-9H-purin-1-ium [ No CAS ]
  • 8
  • [ 106-31-0 ]
  • [ 60-92-4 ]
  • sodium bucladesine [ No CAS ]
  • 9
  • [ 124-19-6 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-Non-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 10
  • [ 4784-77-4 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[1-((E)-But-2-enyl)-6-imino-1,6-dihydro-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 11
  • [ 112-31-2 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-Dec-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 12
  • [ 111-71-7 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-Hept-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 13
  • [ 110-62-3 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-2-Oxo-6-[6-pent-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 14
  • [ 124-13-0 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-Oct-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 15
  • [ 124-25-4 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-2-Oxo-6-[6-tetradec-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 16
  • [ 10416-59-8 ]
  • [ 60-92-4 ]
  • [ 32645-64-0 ]
  • 17
  • [ 100-39-0 ]
  • [ 60-92-4 ]
  • [ 62742-71-6 ]
  • 18
  • [ 100-52-7 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-2-Oxo-6-(6-[1-phenyl-meth-(Z)-ylidene]-amino}-purin-9-yl)-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 19
  • [ 75-07-0 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-Eth-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 20
  • [ 123-38-6 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-2-Oxo-6-[6-prop-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 21
  • [ 123-72-8 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-But-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 22
  • [ 66-25-1 ]
  • [ 60-92-4 ]
  • (4aR,6R,7R,7aS)-6-[6-Hex-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 23
  • [ 60-92-4 ]
  • [ 124-40-3 ]
  • [ 77881-41-5 ]
  • [ 77881-40-4 ]
  • 24
  • [ 60-92-4 ]
  • [ 78-84-2 ]
  • (4aR,6R,7R,7aS)-6-{6-[2-Methyl-prop-(Z)-ylideneamino]-purin-9-yl}-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol [ No CAS ]
  • 25
  • [ 60-92-4 ]
  • [ 98-59-9 ]
  • [ 77056-11-2 ]
  • 26
  • [ 60-92-4 ]
  • [ 74-88-4 ]
  • 1-Methyladenosin 3',5'-cycl Phosphat [ No CAS ]
  • 28
  • [ 60-92-4 ]
  • [ 58-61-7 ]
  • 29
  • [ 73706-11-3 ]
  • [ 60-92-4 ]
  • 31
  • C22H38N6O6P(1+) [ No CAS ]
  • [ 74-88-4 ]
  • [ 58937-08-9 ]
  • [ 50884-82-7 ]
  • [ 60-92-4 ]
  • 32
  • [ 60-92-4 ]
  • [ 3545-76-4 ]
  • 33
  • [ 35231-44-8 ]
  • [ 60-92-4 ]
  • <4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • 34
  • [ 7598-10-9 ]
  • [ 60-92-4 ]
  • (2-Anthraquinonyl)methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • 35
  • [ 60-92-4 ]
  • [ 939-26-4 ]
  • equatorial-2-Naphthylmethyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • axial-2-Naphthylmethyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • 36
  • <4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 72433-26-2 ]
  • [ 60-92-4 ]
  • 38
  • equatorial-(7-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 72433-26-2 ]
  • [ 60-92-4 ]
  • 39
  • axial-(7-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 72433-26-2 ]
  • [ 60-92-4 ]
  • 42
  • [ 58-64-0 ]
  • adenylate-cyclase [ No CAS ]
  • [ 60-92-4 ]
  • 44
  • ATP( disodium-salt) [ No CAS ]
  • [ 60-92-4 ]
  • 46
  • [ 7647-01-0 ]
  • [ 60-92-4 ]
  • acidic ion exchanger [ No CAS ]
  • [ 293304-89-9 ]
  • [ 81158-47-6 ]
  • [ 73-24-5 ]
  • 48
  • [ 60-92-4 ]
  • [ 339291-35-9 ]
  • {4-[6-(6-amino-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-<i>d</i>][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2<i>H</i>-chromen-7-yloxy}-acetic acid <i>tert</i>-butyl ester [ No CAS ]
  • {4-[6-(6-amino-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-<i>d</i>][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2<i>H</i>-chromen-7-yloxy}-acetic acid <i>tert</i>-butyl ester [ No CAS ]
  • 49
  • [ 60-92-4 ]
  • [ 339291-36-0 ]
  • [6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl]methyl ester of cAMP [ No CAS ]
  • [6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl]methyl ester of cAMP [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; acetonitrile; at 60℃; for 24h;Exclusion of light; Example 1 [6,7-Bis(carboxymethoxy)coumarin-4-yl]methyl ester of <strong>[60-92-4]cAMP</strong> A mixture of 1 mmol <strong>[60-92-4]cAMP</strong> and 1.5 mmol 6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl]diazomethane (prepared from commercially available 6,7-dihydroxy-4-methylcoumarin by alkylation with tert-butyl bromoacetate, subsequent conversion to the 6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-carbaldehyde by oxidation with selenium dioxide, reaction of the aldehyde with p-toluenesulfonylhydrazine to form the corresponding p-toluenesulfonylhydrazone, and subsequent conversion to the diazo compound by treatment with triethylamine) in 8 ml DMSO and 32 ml of acetonitrile is stirred for 24 hours at 60 C. in the absence of light. The acetonitrile is removed on a rotatory evaporator and the DMSO and some byproducts are removed by repeated shaking with ether. The residue which includes the [6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl]methyl ester of <strong>[60-92-4]cAMP</strong> is purified using flash chromatography (elution with chloroform/methanol) and/or preparative HPLC (PLRP-S, 10 mum, 250×25 mm i.d., flow rate 10 ml/min, linear gradient 20%-60% B for 70 min, eluant A: water, eluant B: acetonitrile) and optionally separated into the axial and equatorial isomers at the same time. 20 minutes of stirring performed with the pure axial or the pure equatorial form or with a mixture of both forms of the [6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl]methyl ester of <strong>[60-92-4]cAMP</strong> in chloroform/TFA/water (25:74:1; about 2.5 ml per 20 mg) furnishes-after removal of the solvents and lyophilization-the [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester of CAMP as the pure axial or pure equatorial isomer or as a mixture of the isomers. Overall yield: 25% of theoretical amount. Axial isomer: 32P-NMR (DMSO-d6): delta=-5.03; UV: lambdamax (epsilon): 346 (12,000). Equatorial isomer: 32P-NMR (DMSO-d6): delta=-3.26; UV: lambdamax (epsilon): 347 (12,000).
  • 56
  • [ 82156-55-6 ]
  • [ 60-92-4 ]
  • [ 402755-29-7 ]
  • [ 402755-28-6 ]
  • 57
  • [ 82156-57-8 ]
  • [ 60-92-4 ]
  • [ 402755-32-2 ]
  • [ 402755-30-0 ]
  • 58
  • [ 88404-25-5 ]
  • [ 60-92-4 ]
  • equatorial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 402755-34-4 ]
  • 59
  • [ 60-92-4 ]
  • 4-(diazomethyl)-7-(dimethylamino)coumarin [ No CAS ]
  • equatorial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • axial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • 60
  • [ 339291-47-3 ]
  • [ 54711-38-5 ]
  • [ 60-92-4 ]
  • 61
  • [ 339291-37-1 ]
  • [ 54711-38-5 ]
  • [ 60-92-4 ]
  • 62
  • [ 402755-29-7 ]
  • [ 35893-97-1 ]
  • [ 60-92-4 ]
  • 63
  • [ 402755-28-6 ]
  • [ 35893-97-1 ]
  • [ 60-92-4 ]
  • 64
  • [ 402755-32-2 ]
  • [ 60-92-4 ]
  • 4-(hydroxymethyl)-6-methoxycoumarin [ No CAS ]
  • 65
  • [ 402755-30-0 ]
  • [ 60-92-4 ]
  • 4-(hydroxymethyl)-6-methoxycoumarin [ No CAS ]
  • 66
  • equatorial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 60-92-4 ]
  • [ 105567-75-7 ]
  • 67
  • axial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 60-92-4 ]
  • [ 105567-75-7 ]
  • 68
  • equatorial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate [ No CAS ]
  • [ 60-92-4 ]
  • [ 402755-39-9 ]
  • 69
  • [ 402755-34-4 ]
  • [ 60-92-4 ]
  • [ 402755-39-9 ]
  • 70
  • [ 5959-90-0 ]
  • [ 60-92-4 ]
  • [ 61-19-8 ]
  • [ 58-64-0 ]
  • C20H29N10O17P3 [ No CAS ]
  • 71
  • [ 10328-92-4 ]
  • [ 60-92-4 ]
  • 2-Methylamino-benzoic acid (4aR,6R,7R,7aR)-6-(6-amino-purin-9-yl)-2-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl ester [ No CAS ]
  • 72
  • [ 438468-98-5 ]
  • [ 60-92-4 ]
  • [ 438469-00-2 ]
  • [ 438469-01-3 ]
  • 73
  • [ 60-92-4 ]
  • [ 61-19-8 ]
YieldReaction ConditionsOperation in experiment
With bovine serum albumin; In aq. buffer; at 30℃;Enzymatic reaction; General procedure: Time course experiments were performed in PDE buffer + 0.05% (m/v) BSA at a <strong>[60-92-4]cAMP</strong>- or cCMP-concentration of 3 muM. The purified GST-tagged and truncated PDE7A1/2 was added at a concentration of 0.95 mug/ml, corresponding to 210 pmol/(min ml). Crude PDE7A1-containing Sf9 cell lysate was added to yield a final activity of 5 U/ml. The samples were incubated at 30 C under constant shaking. Aliquots were drawn at appropriate times, processed as described for the enzyme screening experiments (Section 2.2) and analyzed by HPLC-MS/MS as described in the Supplementary Methods. In all experiments, the samples were repeatedly subjected to short centrifugations (at least every 30 min) to avoid concentration changes by evaporation- and condensation processes.
With ethylenediaminetetraacetic acid; recombinant N-terminally GST-tagged human cardiac phosphodiesterase PDE3A (484?1141); magnesium chloride; BSA; In aq. buffer; at 30℃; for 0.0333333h;pH 7.5;Enzymatic reaction;Kinetics; Catalytic behavior; General procedure: For the determination of KM and Vmax values of PDE3A mediated <strong>[60-92-4]cAMP</strong> and cUMP hydrolysis, substrate concentrations between 0.1 and 6 muM (<strong>[60-92-4]cAMP</strong>) and between 1muM and 1.5 mM (cUMP) were used in 1× PDE buffer supplemented with 0.05% of BSA. The reaction was started by adding PDE3A to yield a final concentration of 0.1mug/ml and a final sample volume of 50 mul. Negative controls without PDE were run in parallel for each substrate concentration. All samples were run in duplicates and incubated for 15 min (cUMP) or 2 min (<strong>[60-92-4]cAMP</strong>) at 30 C under constant shaking (300 rpm). After that, 40 mul aliquots were drawn, heat-inactivated, and frozen overnight as described in the section about the time course experiments. In the next step, the samples were thawed and centrifuged(15 min, 20,800×g, 4 C) to remove precipitated protein. In case of samples with less than 10 muM of cNMPs, 10mul of the supernatant was diluted 1:4 with purified water. For cNMP concentrations of more than 10muM and less than 0.5 mM, the supernatant was diluted 1:200 (1:50, followed by 1:4) with purified water. Substrate concentrations higher than 0.5 mM were diluted 1:400 (1:100, followed by 1:4). Forty microliters of these dilutions were mixed 1:1 with tenofovir solution(100 ng/ml) to yield a final tenofovir concentration of 50 ng/ml and a final volume of 80 mul. The HPLC-MS/MS measurement was performed as previously described (Monzel et al.2014).
With rhodopsin fused to a C-terminal cyclic nucleotide phosphodiesterase domain; sodium chloride; sodium hydroxide; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; In aq. buffer; at 20℃;pH 6.5;Irradiation; Enzymatic reaction; General procedure: HEK293T cells were transfected with plasmid pCDNA3.1-Rh-PDE by the calcium phosphate method. DMEM/F-12medium contained 0.5 M all-trans-retinal and penicillin andstreptomycin. The cells were harvested after 24 h and washed inbufferA(140mMNaCl, 3mMMgCl2, 50mMHEPES-NaOH,pH6.5). The cells were resuspended with buffer A and homogenizedusing a Potter-Elehjem grinder (Wheaton) and a syringewith a 27-gauge needle. The syringe was filled and drained fivetimes while stirring the homogenate. The protein amount wasdetermined by a BCA protein assay (Thermo Fisher Scientific).Samples were kept in the dark before measurement for at least2 h. Catalytic activity was measured at room temperature in 100l of buffer A with 1.6-1.8 g (in the case of cGMP) or 16-18g (in the case of <strong>[60-92-4]cAMP</strong>) of total protein in a 1.5-ml sampletube. The sample was illuminated with a xenon lamp (MAX-303, Asahi Spectra Co.) through a Y52 filter (7 mW mm2).Reaction was initiated by adding cyclic nucleotides (final concentration100 M). Aliquots were taken out at different timepoints, and the reactions were immediately terminated by adding100 l of 0.1 N HCl and frozen in liquid nitrogen. Afterthawing, the samples were centrifuged to remove the membranesand denatured proteins. Nucleotides (20 l of aliquot)were separated by HPLC (Shimadzu Corp., Kyoto, Japan) with aC18 reversed-phase column (Waters) and 100 mM potassiumphosphate (pH 5.9), 4 mM tetrabutylammonium iodide, and10% (v/v) methanol as eluent (12, 26). Nucleotides were monitoredat 254 nm. Data were evaluated with LabSolutions (Shimadzu).Peak areas were integrated and assigned to the eductcyclic nucleotide based on retention times of correspondingstandard compound.
  • 76
  • [ 56-65-5 ]
  • [ 60-92-4 ]
YieldReaction ConditionsOperation in experiment
With isolated guanylyl cyclase domain of protein rhodopsin-guanylate cyclase double mutant with adenylyl cyclase activity; manganese(ll) chloride; In aq. buffer; for 0.00833333h;pH 7.6;Enzymatic reaction;Catalytic behavior; Kinetics; General procedure: Guanylyl cyclase activity was measured using reversed-phase (RP)-HPLC to follow formation of cGMP and disappearance of GTP. 100-l reactions were prepared in 50 mM Tris buffer, pH7.6, containing 50 mM NaCl and 0.5 mM EDTA. Reactions contained GTP and metal ion (MgCl2 or MnCl2) at the concentrations indicated in the figures and were initiated by addition of enzyme. 20-l aliquots were quenched at specified time points (30 s to 5 h) by combining with an equal volume of 1 N HCl. Precipitated protein was removed with 0.22-m Spin-X centrifugal filters (Corning Costar) by centrifugation at 5000 rpm for 5 min in a table top centrifuge. The samples were then neutralized with 20 l of 1 M potassium phosphate, pH 8, and applied to a 250*2.1-mm ACE5 C18-AR reversed-phase 5mum column connected to an Agilent 1260 Infinity HPLC system with a G136D 1260 multiwave length detector. Nucleotides were separated by isocratic elution with a 100 mM potassium phosphate buffer, pH 6.2, at a flow rate of 0.4 ml/min and monitored by absorbance at 254 nm. Peaks were integrated with OpenLab CDS ChemStation software and compared with peaks from standards for GTP and cGMP of known concentration. Assays for adenylyl cyclase activity were performed identically except that the reaction contained <strong>[56-65-5]ATP</strong> instead of GTP, and the HPLC column running buffer was 100 mM potassium phosphate, pH 6.2, containing 10% (v/v) methanol. The concentration of stock solutions was determined spectrophotometrically using extinction coefficients of 13,700 M-1 cm-1 at 252 nm for GTP, 12,320 M-1 cm-1 at 260 nm for cGMP, 15,400 M-1 cm-1 at 259 nm for <strong>[56-65-5]ATP</strong>, and 15,000 M-1 cm-1 at 260 nm for cAMP. The dependence of activity on enzyme concentration was evaluated through a non-linear least-squares fit (MATLAB) of the rate data to Equation 1 for a reaction in which the only active species is a dimer of the enzyme in a monomer/dimer equilibrium (Eq. 1) where upsilon= reaction rate (muM/s); kcat = turnover number (s-1); E = total enzyme concentration (muM); and KD is the equilibrium dissociation constant for dimerization of the enzyme, defined as KD=[monomer]2 / [dimer] with units of muM. KD and kcat are parameters determined through the fitting process. These reactions contained 10 mM GTP and 20 mM metal ion (Mn2+ or Mg2+), which was saturating for all enzyme concentrations tested.
  • 77
  • ({4-[(2S,4aR,6R,7R,7aS)-6-(6-Amino-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2H-chromen-7-yl}-carboxymethyl-amino)-acetic acid [ No CAS ]
  • [ 876275-37-5 ]
  • [ 60-92-4 ]
  • 78
  • ({4-[(2R,4aR,6R,7R,7aS)-6-(6-Amino-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2H-chromen-7-yl}-carboxymethyl-amino)-acetic acid [ No CAS ]
  • [ 876275-37-5 ]
  • [ 60-92-4 ]
  • 79
  • 7-(bis[(tert-butoxycarbonyl)methyl]amino)-4-(diazomethyl)coumarin [ No CAS ]
  • [ 60-92-4 ]
  • ({4-[6-(6-amino-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-<i>d</i>][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2<i>H</i>-chromen-7-yl}-<i>tert</i>-butoxycarbonylmethyl-amino)-acetic acid <i>tert</i>-butyl ester [ No CAS ]
  • ({4-[6-(6-amino-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-<i>d</i>][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2<i>H</i>-chromen-7-yl}-<i>tert</i>-butoxycarbonylmethyl-amino)-acetic acid <i>tert</i>-butyl ester [ No CAS ]
  • 80
  • [ 60-92-4 ]
  • 9<i>H</i>,9'<i>H</i>-[8,8']bipurinyl-6,6'-diamine [ No CAS ]
  • C10H8N10O2 [ No CAS ]
  • cyclic 3',5'-allantoin ribose monophosphate [ No CAS ]
  • 6,6'-diamino-9<i>H</i>,9'<i>H</i>-[8,8']bipurinyl-2,2'-diol [ No CAS ]
  • 81
  • [ 60-92-4 ]
  • [ 23583-48-4 ]
YieldReaction ConditionsOperation in experiment
76% With bromine; sodium acetate; In water; at 20℃; for 25h; Example 1Preparation of the starting material (Scheme A) :76%The starting material was commercially available <strong>[60-92-4]cAMP</strong>. Bromination on a large scale, as previously described in WO 2005/123755, furnished the 8-bromo derivative. The 2'- OH group of the ribose was subsequently protected by a bulky silyl group to furnish the intermediate silyloxy derivative. Among other things, the silyl group affects relative solubilities. The respective silyl chloride was <n="10"/>employed for the silylation which is best carried out at low temperature to avoid a halogen exchange where the chloride ion would displace the bromide substituent (the chloride ion originates from the silyl chloride reagent) . Low temperature during the reaction and neutralization of the reaction medium before the reaction is worked up avoids halogen exchange. As an alternative the respective silyl triflates could be used to exclude halogen interchange .; Example 48-Bromoadenosine-3 ', 5 ' -cyclic phosphoric acidBromine (15.4 ml, 0.30 mol) was added with stirring to a solution of <strong>[60-92-4]cAMP</strong> (98.8 g, 0.30 mol) and sodium acetate trihydrate (81.6 g, 0.60 mol) in water (1.5 1) over 1 h at room temperature. After 24 h, sodium sulphite was added slowly until disappearance of the dark red colour. The precipitate was collected by filtration, the solid washed with water, 2-propanol and diethyl ether before being dried at reduced pressure. The product was dispersed in wa.ter (500 ml) and dissolved by slow addition of sodium bicarbonate (1 equiv. ) . When all the material had dissolved, small portions of sodium sulphite were added to remove the dark red colour of the solution. Precipitation of the product was effected by dropwise addition of 1.0 M hydrobromic acid under vigorous stirring. The precipitate was collected, washed with water, 2-propanol, diethyl ether and the bright yellow powder dried under high vacuum.Yield 92.0 g (76%) .
With bromine; sodium acetate; In water; at 20℃; for 24h; Example 47 8-Bromoadenosine-3',5'-cyclic phosphoric acid (1); Bromine (15.4 ml, 0.30 mol) was added with stirring to a solution of <strong>[60-92-4]cAMP</strong> (98.8 g, 0.30 mol) and sodium acetate trihydrate (81.6 g, 0.60 mol) in water (1.5 1) over 1 h at room temperature. After 24 h, sodium sulfite was added slowly until disappearance of the dark red colour. The precipitate was collected by filtration, the solid washed with water, isopropyl alcohol and diethyl ether before being dried at reduced pressure. The product was dispersed in water (500 ml) and dissolved by slow addition of sodium bicarbonate (1 equiv. ). When all the material had dissolved, small portions of sodium sulfite were added to remove the dark red colour of the solution. Precipitation of the product was effected by dropwise addition of 1.0 M hydrobromic acid under vigorous stirring. The precipitate was collected, washed with water, isopropyl alcohol, diethyl ether and the bright yellow powder dried under high vacuum; yield 92.0 g (76%). ¹HNMR was in accordance with the literature.
Same Skeleton Products
Historical Records

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[ 60-92-4 ]

Chemical Structure| 102029-77-6

A847864[ 102029-77-6 ]

Adenosine3:5-cyclicmonophosphatetrissalt

Reason: Free-salt