Reaction #652349

ord-90ae0101f6e74a0383a29df67f6e8c24

Reaction equation

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

Reactants

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

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Other46:4524, until the complete consumption of the peptide starting material
  2. 2
    OtherFlash column purification

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06171614B2uspto-grants-2001_01