Hydrochloric Acid → Nicotinamide adenine dinucleotide biotin

HRID 904270

Reaktionsgleichung

Reaktionsgleichung von HRID 904270
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].[CH:17]1[CH:22]=[N+:21]([C@@H:23]2[O:27][C@H:26]([CH2:28][O:29][P:30]([O:33][P:34]([O:37][CH2:38][C@H:39]3[O:43][C@@H:42]([N:44]4[C:48]5[N:49]=[CH:50][N:51]=[C:52]([NH:53]CCN)[C:47]=5[N:46]=[CH:45]4)[C@H:41]([OH:57])[C@@H:40]3[OH:58])([OH:36])=[O:35])([OH:32])=[O:31])[C@@H:25]([OH:59])[C@H:24]2[O-:60])[CH:20]=[C:19]([C:61]([NH2:63])=[O:62])[CH:18]=1.C1(N=C=NCCN2CCOCC2)CCCCC1.Cl>O.[OH-].[Na+].CC(C)=O>[CH:17]1[CH:22]=[N+:21]([C@@H:23]2[O:27][C@H:26]([CH2:28][O:29][P:30]([O:33][P:34]([O:37][CH2:38][C@H:39]3[O:43][C@@H:42]([N:44]4[C:48]5[N:49]=[CH:50][N:51]=[C:52]([NH2:53])[C:47]=5[N:46]=[CH:45]4)[C@H:41]([OH:57])[C@@H:40]3[OH:58])([OH:36])=[O:35])([O-:32])=[O:31])[C@@H:25]([OH:59])[C@H:24]2[OH:60])[CH:20]=[C:19]([C:61]([NH2:63])=[O:62])[CH:18]=1.[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 849981-Cyclohexyl-3-(2-morpholinoethyl)carbodiimideHCID 171548Biotin2×HCID 191523Nicotinamide-6(2-aminoethylamino)purine dinucleotide

Produkt 1

HCID 131711938Nicotinamide adenine dinucleotide biotin

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14798Sodium HydroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A 16 mg quantity of biotin was suspended in 1 ml of water containing 22 mg of nicotinamide 6-(2-aminoethylamino) purine dinucleotide prepared as in Example 1. A few drops of 0.1 N sodium hydroxide was added to aid dissolution of the biotin. A 240 mg quantity of 1-cyclohexyl-3-(2morpholinoethyl)-carbodiimide metho-p-tolulene sulfonate was added to the resulting solution and brought into solution by dropwise addition of 0.1 N hydrochloric acid. The reaction mixture was allowed to incubate at room temperature for 5 hours and was then poured into 10 ml of acetone at 31 10° C. The oil which formed was separated, washed twice with from 5 to 10 ml of ether and dissolved in from 1 to 2 ml of water. The resulting material was purified by electrophoresis on paper as in Example 1. Two fluorescent bands appeared after spraying with sodium cyanide, one having migrated toward the cathode and the other toward the anode. The latter band, which contained the NAD-biotin conjugate, was eluted with water and stored at -20° C.

Aufarbeitung

  1. customThe oil which formed
  2. customwas separated
  3. washwashed twice with from 5 to 10 ml of ether
  4. dissolutiondissolved in from 1 to 2 ml of water
  5. customThe resulting material was purified by electrophoresis on paper as in Example 1
  6. washwas eluted with water
  7. customstored at -20° C.

Quellen und Nachweise

ORD-Eintrag
ord-732a5868497a4986957031eb752fdcf7
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04230797

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