反応 #652349

ord-90ae0101f6e74a0383a29df67f6e8c24

反応方程式

CC(C)[C@H](NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CO)NC(=O)CN)C(=O)O
glycylserylglycylaspartylvaline
OCCCCCCCCCCO
1,10-decanediol
O=C(O)CCCCCCCCCO
10-hydroxydecanoic acid
C(=NC1CCCCC1)=NC1CCCCC1
dicyclohexylcarbodiimide
O=C1CCC(=O)N1O
N-hydroxy-succinimide
→
CCCCCCCCCCO
decanol

反応物

CC(C)[C@H](NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CO)NC(=O)CN)C(=O)O
glycylserylglycylaspartylvaline
OCCCCCCCCCCO
1,10-decanediol
—
peptide
O=C(O)CCCCCCCCCO
10-hydroxydecanoic acid
C(=NC1CCCCC1)=NC1CCCCC1
dicyclohexylcarbodiimide
O=C1CCC(=O)N1O
N-hydroxy-succinimide

試薬

なし

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他46:4524, until the complete consumption of the peptide starting material
  2. 2
    その他Flash column purification

実験手順

Coupling of glycylserylglycylaspartylvaline with 1,10-decanediol. The protected peptide is reacted with 10-hydroxydecanoic acid (Aldrich) in the presence of dicyclohexylcarbodiimide (DCC) (Aldrich) and N-hydroxy-succinimide (Aldrich) according to Bergeron et al. (1981) J. Org. Chem. 46:4524, until the complete consumption of the peptide starting material is confirmed by thin layer chromatography. Flash column purification gives 10-(peptidyloxy) decanol as product, through formation of an amide linkage.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06171614B2uspto-grants-2001_01