Reaktion #70194

ord-f16a58f0cc3047c9a809ef9d9360fae9

Reaktionsgleichung

CCCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-D-Nle-OH
CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O
Boc-D-Phe-OH
O=C(N[C@H](Cc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21
Fmoc-D-Phe-OH
Cc1c(C)c(S(=O)(=O)NC(=N)NCCC[C@@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)c(C)c2c1OC(C)(C)C2
Fmoc-D-Arg(Pbf)-OH
O=C(O)[C@H]1CCCN1C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-D-Pro-OH
→
CCCC[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](N)Cc1ccccc1)C(=O)N[C@H](CCCNC(=N)N)C(=O)N1CCC[C@@H]1C(=O)O
D-Phe-D-Phe-D-Nle-D-Arg-D-Pro-OH

Edukte

—
compound ( 1 )
CCCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-D-Nle-OH
CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O
Boc-D-Phe-OH
O=C(N[C@H](Cc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21
Fmoc-D-Phe-OH
Cc1c(C)c(S(=O)(=O)NC(=N)NCCC[C@@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)c(C)c2c1OC(C)(C)C2
Fmoc-D-Arg(Pbf)-OH
O=C(O)[C@H]1CCCN1C(=O)OCC1c2ccccc2-c2ccccc21
Fmoc-D-Pro-OH
—
amino acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe compound was prepared
  2. 2
    SonstigeFinal purified peptide
  3. 3
    Sonstigeamorphous powder, 140 mg in yield in a synthesis scale of 0.3 mmol

Vorschrift

The compound was prepared according to the procedure described in the synthesis of compound (1). The amino acid derivatives used were Boc-D-Phe-OH, Fmoc-D-Phe-OH, Fmoc-D-Nle-OH, Fmoc-D-Arg(Pbf)-OH, and Fmoc-D-Pro-OH. Final purified peptide: amorphous powder, 140 mg in yield in a synthesis scale of 0.3 mmol. HPLC analysis: tR=20.23 min, purity 99.7%, gradient 10% B to 30% B over 20 min; MS (M+H+): expected molecular ion mass 679.4, observed 679.5.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536131B2uspto-grants-2013_09