L-Tyrosine → HCID 57053813, compound

HRID 1167965Notes

Reaction equation

HRID 1167965 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(O)[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@H](CO)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O.N([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C@H](C(O)=O)CC1C=CC(O)=CC=1.[OH-].[Na+]>CN(C)C=O>[NH2:1][C@H:2]([C:11]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6057L-TyrosineHCID 14798Sodium HydroxideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 46878601HCID 46878601, compound

Product 1

HCID 57053813HCID 57053813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The synthesis of Tyr derivative for iodo-labeling was conducted by the method of Tamura et al. (T. Tamura et al., Anal. Biochem. 216, 335-344 (1994)) (refer to FIG. 4.). That is, 30 μmols of (Gal)3 or (GalNAc)3 were dissolved in 3.6 ml of dimethylformamide, and 1.13 g of Boc-Tyr-NTH (supplied by Sigma) were added thereto. The solution was stirred at 50° C. for 5 hours. After the reaction solution was cooled, 1 N NaOH was added thereto, and a precipitate was removed through centrifugation. The supernatant was added to a Sephadex G-25 column (supplied by Pharmacia) which had been equilibrated with 1% (w) of pyridine and acetic acid to obtain a Tyr-Boc derivative fraction monitored at 280 nm. The fraction obtained was freeze-dried, and then dissolved again in a 0.1% TFA solution. The solution was purified through reversed-phase HPLC using an “Inertsil ODS-2” column (4.6×150 mm, supplied by GL Science Inc.) to form 14.7 mg of a Tyr-Boc derivative ((Gal)3-Tyr-Boc) and 28.9 mg of a Tyr-Boc derivative ((GalNAc)3-Tyr-Boc) having a peak purity of 90% or more. The structures of the products were identiried through electrospray ionization mass spectrometry (ESI-MS).

Workup

  1. temperatureAfter the reaction solution was cooled
  2. customa precipitate was removed through centrifugation
  3. additionThe supernatant was added to a Sephadex G-25 column (supplied by Pharmacia) which

Sources & evidence

ORD record
ord-37cb158a7fd449e6841fe9df4490a9d6
Source dataset
uspto-grants-2003_09
Patent number
US06620916B1

Reaction notes

Loading…