Reaktion #364799

ord-de74687018da4a6989aa8c9929cb9295

Reaktionsgleichung

C[C@@H](NC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O
biotinyl-D-alanine
O=C1CCC(=O)N1O
N-hydroxysuccinimide
C[C@@H](N)C(=O)O
D-alanine
C[C@@H](N)C(=O)O
D-alanine
CCN=C=NCCCN(C)C.Cl
1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride
O=C1CCC(=O)N1O
NHS
Nc1ccccc1.O=C(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1
DOTA aniline
→
O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21.O=C(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1
desired product
O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21.O=C(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1
DOTA Biotin

Edukte

C[C@@H](NC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O
biotinyl-D-alanine
O=C1CCC(=O)N1O
N-hydroxysuccinimide
C[C@@H](N)C(=O)O
D-alanine
—
biotin-NHS ester
C[C@@H](N)C(=O)O
D-alanine
CCN=C=NCCCN(C)C.Cl
1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride
O=C1CCC(=O)N1O
NHS
Nc1ccccc1.O=C(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1
DOTA aniline

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The D-alanine-linked conjugate was prepared by first coupling D-alanine (Sigma Chemical Co.) to biotin-NHS ester. The resultant biotinyl-D-alanine was then activated with 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDCI) and N-hydroxysuccinimide (NHS). This NHS ester was reacted in situ with DOTA-aniline to give the desired product which was purified by preparative HPLC.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06358490B2uspto-grants-2002_03