, used in a number of different ways.
- Relative stereodescriptors used in carbohydrate nomenclature to describe the configuration
at the anomeric carbon by relating it to the anomeric reference atom. For simple
cases the anomeric reference atom is the same as the configurational reference
atom. Thus in α-d-glucopyranose the reference atom is C-5 and the
OH at C-1 is on the same side as the OH at C-5 in the Fischer projection.
- Relative stereodescriptors used by Chemical Abstracts Service to describe the configuration
of a cyclic molecule (including suitable polycyclic systems) with several
stereogenic centres whereby the α side of the reference plane is the side on
which the substituent with CIP priority lies at the
lowest numbered stereogenic centre. The other side is β.
- Absolute stereodescriptors originally devised for steroid nomenclature. However in
this sense it is only meaningful if there is an agreed absolute configuration and orientation of the structure so as to define the plane and which way up the molecule
is represented. Substituents above the plane of the
steroid are described as β and are shown as a solid line ( or ); those below the plane are described as α and are shown by a broken line ( or ). The
extension of this system to tetrapyrroles has been documented and it has been widely used elsewhere.
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC
on page 2197
See also: PAC, 1989, 61, 1783 (Nomenclature of steroids (Recommendations 1989))
1783 PAC, 1987, 59, 779 (Nomenclature of tetrapyrroles (Recommendations 1986))
on page 779
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by
A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications,
Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-)
created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8.