New hydrophobic vitamin B12 derivatives via ring-opening reactions of c-lactone.
A selective synthesis of new hydrophobic cobalamin derivatives bearing two different spacers has been accomplished via ring-opening reaction of c-lactone. The reaction of c-lactone with various amines afforded three types of amides (a, b, and c) depending on the reaction conditions. The structure of lactone b was determined by the X-ray analysis confirming the position of ring closure. It also reveals the presence of a hydrogen bond between the terminal hydroxy group and one of the axial cyanide ligands.
ó Proinsias
Keith
K
Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Sessler
Jonathan L
JL
Kurcoń
Sylwester
S
Gryko
Dorota
D
D018360:Crystallography, X-Ray; D057927:Hydrophobic and Hydrophilic Interactions; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry; D014805:Vitamin B 12 / Q000031:analogs & derivatives*
D007783:Lactones; D013141:Spiro Compounds; D014805:Vitamin B 12