An isolable acyclic hemiacetal of ansamitocin P-3.
Magn Reson Chem
; 50(3): 256-9, 2012 Mar.
Article
em En
| MEDLINE
| ID: mdl-22374862
ABSTRACT
During impurity analysis of maytansinol (2), produced from the reduction of ansamitocin P-3 (AP-3, 1), a surprisingly stable acyclic hemiacetal (4) was isolated. A combination of 1D and 2D NMR experiments, along with liquid chromatography-mass spectrometry data was used to confirm the structure. Comparison of NMR data to the previously reported bridged acetal (3), a by-product of AP-3 reduction, supports reassignment of the latter to the former. Additionally, ROESY data, in conjunction with minimum energy calculations, support intramolecular hydrogen bonding that is involved in stabilizing the hemiacetal. This report adds another example to the very short list of isolable acyclic hemiacetals.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Maitansina
Idioma:
En
Revista:
Magn Reson Chem
Ano de publicação:
2012
Tipo de documento:
Article