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Recall that a point can be considered a sterocenter with a minimum of three attachment points; stereocenters can be either sp 3 or sp 2 hybridized, as long as the interchanging any two different groups creates a new stereoisomer. This means that although all chirality centers are stereocenters, not every stereocenter is a chirality center.
In a configurational isomer, the lowest priority group (most times hydrogen) is positioned behind the plane or the hatched bond going away from the reader. The highest priority group will have an arc drawn connecting to the rest of the groups, finishing at the group of third priority. An arc drawn clockwise, has the rectus (R) assignment.
In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. [1] [2] The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically ...
The groups COOH, R, NH 2 and H (where R is the side-chain) are arranged around the chiral center carbon atom. With the hydrogen atom away from the viewer, if the arrangement of the CO→R→N groups around the carbon atom as center is counter-clockwise, then it is the L form. [14] If the arrangement is clockwise, it is the D form. As usual, if ...
Chiral molecules will usually have a stereogenic element from which chirality arises. The most common type of stereogenic element is a stereogenic center, or stereocenter. In the case of organic compounds, stereocenters most frequently take the form of a carbon atom with four distinct (different) groups attached to it in a tetrahedral geometry.
Enantiotopic groups are identical and indistinguishable except in chiral environments. For instance, the CH 2 hydrogens in ethanol (CH 3 CH 2 OH) are normally enantiotopic, but can be made different (diastereotopic) if combined with a chiral center, for instance by conversion to an ester of a chiral carboxylic acid such as lactic acid, or if coordinated to a chiral metal center, or if ...
The chiral C-atom most remote from the group with the highest priority is used for the assignment of D- or L-. If the residue located on this carbon atom (usually an OH group) points to the left, the molecule originates from the L-series. If the residue points to the right, the descriptor D- is used. [41]
That is, the groups hanging off the chain at the α-carbon are what give amino acids their diversity. These groups give the α-carbon its stereogenic properties for every amino acid except for glycine. Therefore, the α-carbon is a stereocenter for every amino acid except glycine. Glycine also does not have a β-carbon, while every other amino ...