310-39 - Organic Lecture Series CH 310 N LECTURE 39...

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Organic Lecture Series 1 CH 310 N LECTURE 39 Textbook Assignment: Chapter 25- Carbohydrates Homework (for credit): POW 13 (Due 5/2) Today’s Topics: Carbohydrates-structure; chirality; nomenclature. Notice & Announcements: XM3: Grades posted Selected Topics from Chapters 25, 26 & 27 for the rest of the course. Use lecture notes for topics. Organic Lecture Series 2 Carbohydrates Carbohydrates Chapter 24
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Organic Lecture Series 3 Cyclic Structure • Monosaccharides have hydroxyl and carbonyl groups in the same molecule and exist almost entirely as five- and six- membered cyclic hemiacetals anomeric anomeric carbon: carbon: the new stereocenter created as a result of cyclic hemiacetal formation anomers anomers : carbohydrates that differ in configuration at their anomeric carbons Organic Lecture Series 4 Haworth Projections Haworth Projections Haworth projections – five- and six- membered hemiacetals are represented as planar pentagons or hexagons, viewed through the edge – they are most commonly written with the anomeric carbon on the right and the hemiacetal oxygen to the back right O CH 2 OH H OH OH H OH OH Anomeric Carbon H H OH H H HOH 2 C OH OH H H O Anomeric Carbon
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Organic Lecture Series 5 O CH 2 OH H OH OH H OH H Anomeric Carbon H OH 1 6 5 4 3 2 a-D-Glucopyranose a-D-Glucose a Organic Lecture Series 6 OH H H CH 2 OH OH OH H H O Anomeric Carbon 5 4 3 2 1 a-D-Ribofuranose a-D-Ribose a
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Organic Lecture Series • Haworth projections the designation &- means that the - OH on the anomeric carbon is cis to the terminal -CH 2 OH; &- means that it is trans to the terminal -CH 2 OH O CH 2 OH H OH OH H OH H Anomeric Carbon H OH O CH 2 OH H OH OH H OH OH Anomeric Carbon H H & a Organic Lecture Series 8 Haworth Projections Haworth Projections CHO OH H H HO H H CH 2 H H H H OH( β ) H 2 O C H H H H 2 O H α ) H H H H H 2 O D-Glucose β -D-Glucopyranose ( β -D-Glucose) α ( α -D-Glucose ) anomeric carbon +
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310-39 - Organic Lecture Series CH 310 N LECTURE 39...

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