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Bicarbonate Ion → ((2R,3S,4R,5R)-5-(6-Amino-8-((2-aminoethyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

HRID 414163
Notes
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Reaction equation

HRID 414163 reaction equation
[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[C:21]3[N:20]=[CH:19][N:18]=[C:16]([NH2:17])[C:15]=3[N:14]=[C:13]2Br)[C@H:9]([OH:23])[C@@H:8]1[OH:24])([OH:4])([OH:3])=[O:2].[CH2:25]([NH2:28])[CH2:26][NH2:27].[OH-].[Na+].C(=O)(O)[O-]>O>[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[C:21]3[N:20]=[CH:19][N:18]=[C:16]([NH2:17])[C:15]=3[N:14]=[C:13]2[NH:27][CH2:26][CH2:25][NH2:28])[C@H:9]([OH:23])[C@@H:8]1[OH:24])([OH:4])([OH:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 1681208-Bromo-9-(5-O-phosphonopentofuranosyl)-9H-purin-6-amine

Product 1

HCID 22823186((2R,3S,4R,5R)-5-(6-Amino-8-((2-aminoethyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture consisting of 2.2 mmol 8-bromoadenosine-5'-monophosphate, prepared according to the method described in Arch. Biochem. Biophys. 163: 561-9(1974), 66 mmol ethylenediamine and 25 ml water was heated in an oil bath at 140° for 2 hr. The cooled mixture was adjusted to pH 11.5 with sodium hydroxide and passed into a 2.5×55 cm column of Dowex 1×8 (200-400 mesh, bicarbonate form). The column was washed with 300 ml water and then with a linear gradient generated with 3 liters water and 3 liters 0.5M ammonium bicarbonate. The absorbance of the effluent at 254 nm was monitored and a major peak of absorbing material eluted between 4.6 and 5.8 liters of the gradient.

Workup

  1. customprepared
  2. washThe column was washed with 300 ml water
  3. washa major peak of absorbing material eluted between 4.6 and 5.8 liters of the gradient

Sources & evidence

ORD record
ord-abfc018b68cc4b24ab2fa6fd05fcb8c1
Source dataset
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04791055

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes