Biomolecules and Chemistry in Everyday Life - Result Question 25

26. The Fischer presentation of $D$-glucose is given below.

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-465_jpg_height_315_width_212_top_left_y_1926_top_left_x_1533.jpg"width="100">

The correct structure(s) of $\beta$-L-glucopyranose is (are)

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-465_jpg_height_278_width_654_top_left_y_2335_top_left_x_1234.jpg"width="400">

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Answer:

Correct Answer: 26. (d)

Solution:

  1. (d) A pyranose ring is a $6$ membered ring having $5$ carbon atoms and one oxygen atom. In glucose, it is formed by the reaction between $>C=O$ group at position $1$ and $-OH$ group at 5 th carbon atom. In general reaction between $>C=O$ group

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/snip_images_7zYMwm4LP1y1L3k13GFkmUGC1NhThPkLuitObY76grY_original_fullsize_png.jpg"width="400"/>

The product formed in called hemiacetal

(if $>C=O$ group belongs to an aldehyde) or hemiketal (if $>C=O$ group belongs to a ketone). $L$ - glucose has the mirror image configuration of D-glucose i.e.,

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-473_jpg_height_442_width_480_top_left_y_385_top_left_x_1376.jpg"width="300"/>

So, $\beta$ - $L$ glucopyranose is formed as

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-473_jpg_height_279_width_732_top_left_y_888_top_left_x_1253.jpg"width="400"/>

The $\alpha$-$L$-glucopyranose has configurational change at $C _1$ only and looks like

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-473_jpg_height_264_width_528_top_left_y_1257_top_left_x_1355.jpg"width="400"/>



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