Reaktion #1525

ord-3bb66da6f37b43aebd4a5504e234b1f4

Reaktionsgleichung

N[C@@H](CS)C(=O)O
L-cysteine
CC(C)[C@H](N)C(=O)O
L-valine
CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-].[K+]
penicillin
→
CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O
isopenicillin N

Edukte

—
tripeptide
—
amino acids L-5-amino-5-carboxypentanoic acid
—
tripeptide
N[C@@H](CS)C(=O)O
L-cysteine
CC(C)[C@H](N)C(=O)O
L-valine
CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-].[K+]
penicillin

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The first two steps in the biosynthesis of penicillin in P. chrysogenum are the condensation of the three amino acids L-5-amino-5-carboxypentanoic acid (L-α-aminoadipic acid) (A), L-cysteine (C) and L-valine (V) into the tripeptide LLD-ACV, followed by cyclization of this tripeptide to form isopenicillin N. This compound contains the typical β-lactam structure.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726032uspto-grants-1998_03