Reaktion #338498

ord-73c73a56b2d444b7857252e72f7b484d

Reaktionsgleichung

CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Lys(Boc)-OH
CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)O
H-Lys(Boc)-2-chlorotrityl resin
O=C(O)C(F)(F)F
TFA
CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Val-OH
→
CC(C)[C@H](NC(=O)[C@@H](N)CCCCN)C(=O)N[C@@H](CCCCN)C(=O)O
Lys-Val-Lys-OH

Edukte

CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Lys(Boc)-OH
—
peptide
CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)O
H-Lys(Boc)-2-chlorotrityl resin
O=C(O)C(F)(F)F
TFA
CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Val-OH

Reagenzien

Keine

Lösungsmittel

CCOCC
Et2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed
  2. 2
    Sonstigepurified by prep
  3. 3
    SonstigeHPLC after drying
  4. 4
    workup.ADDITIONThe substance is diluted in 30 ml of dioxan
  5. 5
    workup.ADDITIONwater=4:6, treated overnight with 2.0 g of BioRad resin (acetate form)
  6. 6
    Filtrationfiltered

Vorschrift

The protective peptide is built on 1.00 g (0.80 mmol) of H-Lys(Boc)-2-chlorotrityl resin using Fmoc-Val-OH, Fmoc-Lys(Boc)-OH and Palm-OSu. The resin is treated for 30 min with 8 ml of TFA 95% and the solution is instilled in 100 ml of Et2O. The precipitate is sucked off, washed and purified by prep. HPLC after drying. The substance is diluted in 30 ml of dioxan:water=4:6, treated overnight with 2.0 g of BioRad resin (acetate form), filtered, rotated and lyophilized. Yield: 110 mg (0.15 mmol, 19%)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07863417B2uspto-grants-2011_01