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    Michael Blanco
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    The document discusses the configurations of aldoses (sugars with an aldehyde functional group). It notes that all naturally occurring sugars are D-sugars, which have the hydroxyl group on the terminal stereocenter pointing to the right in Fischer projections. The number of D- and L-sugars is related by 2n, with each new type of sugar built by inserting a hydrogen-carbon-hydroxyl or hydroxyl-carbon-hydrogen above the closest stereocenter in the framework of the sugar with one less carbon. Fischer projections of several D-aldose sugars are shown to illustrate this.

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    Organic Chemistry notes.

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    The document discusses the configurations of aldoses (sugars with an aldehyde functional group). It notes that all naturally occurring sugars are D-sugars, which have the hydroxyl group on the terminal stereocenter pointing to the right in Fischer projections. The number of D- and L-sugars is related by 2n, with each new type of sugar built by inserting a hydrogen-carbon-hydroxyl or hydroxyl-carbon-hydrogen above the closest stereocenter in the framework of the sugar with one less carbon. Fischer projections of several D-aldose sugars are shown to illustrate this.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    23 views1 page

    Organic Chemistry

    Uploaded by

    Michael Blanco
    The document discusses the configurations of aldoses (sugars with an aldehyde functional group). It notes that all naturally occurring sugars are D-sugars, which have the hydroxyl group on the terminal stereocenter pointing to the right in Fischer projections. The number of D- and L-sugars is related by 2n, with each new type of sugar built by inserting a hydrogen-carbon-hydroxyl or hydroxyl-carbon-hydrogen above the closest stereocenter in the framework of the sugar with one less carbon. Fischer projections of several D-aldose sugars are shown to illustrate this.

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    © All Rights Reserved
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    Carbohydrates-8

    Configurations of the Aldoses: D- and L-Sugars

    108B
    Carbos-8

    -All naturally occurring sugars are D-sugars = R configuration at the terminal stereogenic C
    -Fischer Projections: D-sugar = OH on terminal (bottom) stereogenic C points to the right;
    L-sugar = OH on terminal (bottom) stereogenic C points to the left;
    -Note the 2n relationship between number of each type of sugar
    Each new type of sugar is "built"
    by inserting H-C-OH and HO-C-H
    "above" the stereogenic C closest to the C=O
    in the framework of the sugar containing 1-C less

    The D-Aldoses
    H
    Insert H-C-OH here
    HO-C-H

    O
    OH

    CH2OH

    D-Glyceraldehyde
    H

    OH

    HO

    OH

    D-Threose
    (2S, 3R )

    OH

    HO

    OH

    OH

    HO

    OH

    OH

    CH2OH

    HO

    OH

    HO

    OH

    OH

    OH

    HO

    OH

    OH

    OH

    OH

    HO

    OH

    OH

    OH

    OH

    D-Altrose
    ( 5R )

    OH

    CH2OH

    HO

    CH2OH

    D-Glucose D-Mannose
    ( 5R )
    ( 5R )

    H
    OH
    CH2OH

    D-Gulose
    ( 5R )

    HO

    OH HO

    OH

    HO

    D-Allose
    ( 5R )

    OH

    CH2OH

    HO
    H

    OH
    CH2OH

    D-Lyxose
    ( 4R )

    D-Xylose
    ( 4R )

    CH2OH

    CH2OH

    D-Arabinose
    ( 4R )

    OH

    D-Erythrose
    ( 2R, 3R )

    H
    CH2OH

    CH2OH

    CH2OH

    D-Ribose
    ( 4R )

    OH

    HO

    OH HO

    HO

    HO

    HO

    H
    OH
    CH2OH

    D-Idose
    ( 5R )

    OH
    CH2OH

    OH
    CH2OH

    D-Galactose D-Talose
    ( 5R )
    ( 5R )

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