Molecule
MoleculePlot
MoleculeModify
AtomLabels

Chemistry

Enumerating Stereoisomers

List all the possible stereoisomers of a sugar molecule with four stereogenic centers

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Start with a molecule of D-glucose:

In[1]:=

glucose=Molecule["D-glucose"]

Out[1]=

Molecule

Formula:

Atoms: 24 Bonds: 23



Show that there are four possible chiral centers. This means that there are

=16

stereoisomers:

In[2]:=

centers=glucose["PossibleStereocenters"]

Out[2]=

{3,5,7,9}

Get a plot of the molecule and highlight the centers:

In[3]:=

MoleculePlot[glucose,centers]

Out[3]=

Use the

"AtomChirality"

property to get the configuration at all the stereocenters:

In[4]:=

glucose[{"AtomChirality",centers}]

Out[4]=

{R,S,R,R}

Use

MoleculeModify

to set the chirality at each center:

In[5]:=

MoleculePlot[MoleculeModify[glucose,{"SetAtomChirality",Thread[centers{"R","R","R","R"}]}],AtomLabels"AtomChirality"]

Out[5]=

Make a table of the 16 different configurations, enumerating the possibilities using

Tuples

In[6]:=

sugars=Table[MoleculeModify[glucose,{"SetAtomChirality",Thread[centersconfiguration]}],{configuration,Tuples[{"R","S"},4]}];

Use

MoleculeName

to look up the chemical name for the stereoisomers:

In[7]:=

MoleculeName/@sugars

Out[7]=

{aldehydo-D-allose,aldehydo-L-talose,aldehydo-D-gulose,aldehydo-L-mannose,(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal,aldehydo-L-idose,aldehydo-D-galactose,aldehydo-L-altrose,aldehydo-D-altrose,aldehydo-L-galactose,aldehydo-D-idose,aldehydo-L-glucose,aldehydo-D-mannose,aldehydo-L-gulose,aldehydo-D-talose,aldehydo-L-allose}

Plot all the glucose stereoisomers:

In[8]:=

GridPartitionMoleculePlot#,

&/@sugars,UpTo[3]

Out[8]=

Related Symbols

Molecule
MoleculePlot
MoleculeModify
AtomLabels

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Contributed by: Wolfram Staff

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Enumerating Stereoisomers

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