Reaktion #1376515

ord-38c117d6d4854ea7ad460c44f7245cf8

Reaktionsgleichung

N[C@@H](CS)C(=O)O
cysteine
O=C(O)[C@@H]1CCCN1
H-Pro
O=C[C@@H]1CCCN1C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Pro-Wang resin
C1CCNCC1.CN(C)C=O
piperidine DMF
C(=NC1CCCCC1)=NC1CCCCC1.On1nnc2ccccc21
DCCI HOBt
OCc1ccc(OCc2ccccc2)cc1
p-benzyloxybenzyl alcohol
O=C(O)[C@@H]1CCCN1C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Pro-OH
→
O=C(N[C@@H](CSC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)O)OCC1c2ccccc2-c2ccccc21
Fmoc-Cys(Trt)-Pro

Edukte

—
peptide
N[C@@H](CS)C(=O)O
cysteine
O=C(O)[C@@H]1CCCN1
H-Pro
O=C[C@@H]1CCCN1C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Pro-Wang resin
C1CCNCC1.CN(C)C=O
piperidine DMF
C(=NC1CCCCC1)=NC1CCCCC1.On1nnc2ccccc21
DCCI HOBt
OCc1ccc(OCc2ccccc2)cc1
p-benzyloxybenzyl alcohol
O=C(O)[C@@H]1CCCN1C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-Pro-OH

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter removal of the solvent Fmoc-Pro-Wang resin
  2. 2
    Sonstigeis obtained

Vorschrift

0.6 g of Fmoc-Pro-OH is dissolved in 100 ml of dichloromethane, 1.2 equivalents of Wang resin (p-benzyloxybenzyl alcohol resin) are added, and the mixture is stirred at room temperature for 12 hours. After removal of the solvent Fmoc-Pro-Wang resin is obtained. In a peptide synthesizer Fmoc-Cys(Trt)-OH is condensed with H-Pro-Wang resin [liberation from Fmoc-Pro-Wang resin using piperidine/DMF (20% strength)], using a three-fold excess of the protected cysteine. The coupling is carried out at room temperature in DCCI/HOBt, to give Fmoc-Cys(Trt)-Pro-Wang resin. Subsequent treatment with piperidine/DMF (20% strength) again gives H-Cys(Trt)-Pro-Wang resin.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05747457uspto-grants-1998_05