2'-Deoxyadenosine-5'-monophosphate

Base Information

• Chemical Name: 2'-Deoxyadenosine-5'-monophosphate
• CAS No.: 653-63-4
• Deprecated CAS: 75688-15-2,87578-08-3,29576-96-3
• Molecular Formula: C10H14N5O6P
• Molecular Weight: 331.225
• Hs Code.: HOSPHATE HYDRATE PRODUCT IDENTIFICATION
• European Community (EC) Number: 211-503-1
• UNII: VFR8I97ORM
• DSSTox Substance ID: DTXSID901034859
• Nikkaji Number: J205.943F
• Wikipedia: Deoxyadenosine_monophosphate
• Wikidata: Q1874427
• Metabolomics Workbench ID: 37495
• ChEMBL ID: CHEMBL1206239
• Mol file: 653-63-4.mol

Synonyms:2'-deoxy-5'-adenosine monophosphate;2'-deoxy-5'-adenosine monophosphate, ammonium salt;2'-deoxy-5'-adenosine monophosphate, disodium salt;2'-deoxyadenosine-5'-monophosphate;2'deoxy-5'-AMP;dAMP cpd;deoxyadenosine monophosphate;deoxyadenylate

Chemical Property of 2'-Deoxyadenosine-5'-monophosphate

Chemical Property:

• Appearance/Colour: Crystalline
• Melting Point: 148 °C
• Boiling Point: 753.527 °C at 760 mmHg
• PKA: 1.86±0.10(Predicted)
• Flash Point: 409.518 °C
• PSA: 175.65000
• Density: 2.174 g/cm³
• LogP: -0.25260
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly)
• Water Solubility.: Soluble in 1N ammonium hhydroxide (50 mg/ml) and water.
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 331.06817018
• Heavy Atom Count: 22
• Complexity: 452

Purity/Quality:

98% ^*data from raw suppliers

2′-Deoxyadenosine 5′-monophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)N)COP(=O)(O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)COP(=O)(O)O)O
• Description: 2’-Deoxyadenosine-5''-monophosphate is a derivative of the nucleic acid, AMP, in which the hydroxyl group on the 2'' carbon of the pentose has been reduced to a hydrogen atom. It has been used in the synthesis of novel photoaffinity labels for incorporation into DNA and to study adenosine-based interactions during DNA synthesis and DNA damage.
• Uses: 2’-Deoxyadenosine 5’Monophosphate is the first nucleotide of the phi 29 DNA.

Technology Process of 2'-Deoxyadenosine-5'-monophosphate

There total 25 articles about 2'-Deoxyadenosine-5'-monophosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.1%

2'-deoxyadenosine-5'-phosphorimidazolide → C10H13FN5O5P (143415-97-8) + 2'-deoxyadenosine-5'-monophosphoric acid (653-63-4)

Guidance literature:

With water; lithium fluoride; at 25 ℃; pH=8.7; Reagent/catalyst; pH-value;

DOI:10.1016/j.tetlet.2014.01.051

Reference yield: 72.0%

2'-deoxy-D-adenosine (958-09-8,7005-15-4) → 2'-deoxyadenosine-5'-monophosphoric acid (653-63-4)

Guidance literature:

2'-deoxy-D-adenosine; With trichlorophosphate; at 20 ℃; for 0.15h; Flow reactor; Green chemistry;

With water; at 20 ℃; Temperature; chemoselective reaction; Flow reactor; Green chemistry;

DOI:10.1021/op5002066

Reference yield:

AppTTTT → thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1) + 2'-deoxyadenosine-5'-monophosphoric acid (653-63-4)

Guidance literature:

With venom phosphodiesterase;

DOI:10.1016/S0040-4039(01)90351-X

upstream raw materials:

phosphoric acid monophenyl ester

2'-deoxy-D-adenosine

deoxyadenosine-5'-trityloxyethylaminophosphate

N⁶-benzoyldeoxyadenosine 5'-phosphate

Downstream raw materials:

1,N⁶-etheno-2'-deoxyadenosine 5'-monophosphate

dATP

2’-chloro-2’-deoxyadenosine monophosphate

5’-O-[({(1S)-3-(benzyloxy)-1-[({(1S)-3-(benzyloxy)-1-[(benzyloxy)carbonyl]-3-oxopropyl}amino)carbonyl]-3-oxopropyl}amino)hydroxyphosphinyl]-2’-deoxyadenosine

Refernces

• 1、 Harnett, Sara P.,Lowe, Gordon. "Stereochemical Evidence for Monomeric Thiometaphosphate as an Intermediate in the Hydrolysis of (Rp) and (Sp)-Deoxyadenosine 5'--β-thiodiphosphate". . p. 1416 - 1418. Retrieved 1987.
• 2、 -. "Catalysts for reversing formaldehyde adducts and crosslinks". Paragraph 0073. . Retrieved 2019/01/10.
• 3、 Serra, Immacolata,Conti, Silvia,Piskur, Jure,Clausen, Anders R.,Munch-Petersen, Birgitte,Terreni, Marco,Ubiali, Daniela. "Immobilized Drosophila melanogaster deoxyribonucleoside kinase (DmdNK) as a high performing biocatalyst for the synthesis of purine arabinonucleotides". . p. 563 - 570. Retrieved 2014/05/20.