Reaktion #464193

ord-ce11cc3f5b5141b0ab6f19c147ec639f

Reaktionsgleichung

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
CNCC(=O)O
N-methyl glycine
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
CNCC(=O)O
N-methyl-glycine
C[C@@H](N)C(=O)O
D-alanine
→
CNCC(=O)C(CCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O
N-methyl glycyl-biotin

Edukte

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
—
biotin-NHS ester
CNCC(=O)O
N-methyl glycine
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
CNCC(=O)O
N-methyl-glycine
C[C@@H](N)C(=O)O
D-alanine

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF
CCN(CC)CC
triethylamine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas prepared by an analogous method to

Vorschrift

The N-methyl glycine-linked DOTA-biotin conjugate was prepared by an analogous method to that used to prepare D-alanine-linked DOTA-biotin conjugates. N-methyl-glycine (trivial name sarcosine, available from Sigma Chemical Co.) was condensed with biotin-NHS ester in DMF and triethylamine to obtain N-methyl glycyl-biotin. N-methyl-glycyl biotin was then activated with EDCI and NHS. The resultant NHS ester was not isolated and was condensed in situ with DOTA-aniline and excess pyridine. The reaction solution was heated at 60° C. for 10 minutes and then evaporated. The residue was purified by preparative HPLC to give [(N-methyl-N-biotinyl)-N-glycyl]-aminobenzyl-DOTA.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06022966uspto-grants-2000_02