Organic Chemistry For Nurse Students
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1 rganic Chemistry For Nurse Students Carbohydrate 20% Lipids Amino acids and proteins Nucleic acids โดย ผศ.ดร น ชน ภา นะนท วงศ ภาคว ชาเคม คณ ว ทยาศาสตร มหาว ทยาละยเช ยงใหม
2 ปร กอบด วย C, แล hydrate of cabon Carbohydrates ส ตรทะ วไปเป น C x ( 2 ) y ปร กอบด วยหม คาร บอน ล (C=) 1 หม แล ไฮดรอกซ ล () หลายหม C C = polyhydroxyaldehydes = polyhydroxyketones
3 ก 1. (Monosaccharides): ก carbon 3 9 ก ก + 2 ก ก 2. ก (ligosaccharides): ก 2 10 ก + 2 +
4 1.3. (Polysaccharides): ก ก
5 C n 2n n Monosaccharides 1 C C 2 C 2 C C 2
6 A. ก ก ก ก ก ose ก ก aldehyde ก aldose ketone ก ketose Monosaccharide C 2 C C 2 3C ก triose 5C ก pentose 4C ก tetrose 6C ก hexose
7 ก ก ก C C 2 Aldotriose C C 2 Aldohexose C C 2 Aldopentose C 2 C C 2 Ketohexose
8 โมโนแซ คคาไรด ท พบ ค อ pentose (C ) แล hexose (C ) C C 2 C C 2 C 2 C 2 C C 2 D-Ribose D-Xylulose D-Xylose C C 2 C C C 2 C 2 D-Glucose D-Fructose D-galactose
9 B. D- L- D- & L- Aldose - Aldose ท เล กท ส ดค อ glyceraldehyde - ม 1 chiral C จ งม 2 steroisomers ท เป น enatiomer กะน (S) S)-2,3 2,3-dihydroxypropanol (L-glyceraldehyde glyceraldehyde) (R) R)-2,3 2,3-dihydroxypropanol (D-glyceraldehyde glyceraldehyde) L D
10 D- & L- Ketose Ketose ท เล กท ส ดค อ dihydroxyacetone C 2 C C 2 ไม ม chiral carbon ในโมเลก ล แต ถ า ketose ท ม #C > 3 atoms จ ม chiral carbon เช น C 2 C C C 2 ketotetrose ได จากการเต มหม -C- เข าไปใน ketotriose
11 -C- C 2 C C 2 dihydroxyacetone -C- C 2 C 2 C C C 2 D-erythrulose C C C 2 L-erythrulose
12 การเร ยกสเทอร โอไอโซเมอร ของน าตาล ให พ จารณา chiral C ท คาร บอนต าแหน งส งส ด ถ าหม - อย ขวาม อ D- isomer ถ าหม - อย ซ ายม อ L-isomer C 2 C C 2 D-ketohexose C 2 C C 2 L-aldopentose
13 โมโนแซ คคาไรด ท เป น stereoisomer กะน เป นได ทะ ง enantiomer แล diasteroisomer C C C 2 C 2 Enantiomer C C C 2 C 2 Diasteroisomer โมเลก ลท เป น diastereoisomer จ ม ไคระลคาร บอนบางต าแหน งจ ต างกะน บางต าแหน งเหม อนกะน อ พ เมอร (epimer epimer) อ โน โนเมอร (anomer anomer)
14 อ พ เมอร (epimer epimer) ม ไคระลคาร บอนต างกะนเพ ยงต าแหน งเด ยว นอกนะ นเหม อนกะนหมด C C C C C 2 C 2 C 2 C 2 D-glucose D-galactose D-ribose D-arabinose
15 อ โน โนเมอร (anomer anomer) ไอโซเมอร ของโมโนแซ คคาไรด ท ม โครงสร างเป นวง โดยคาร บอนท เป นหม คาร บอน ลเด ม จ เปล ยนเป นไคระลคาร บอนใหม ท ม การ จะดตะวของหม - ท ต างกะน จ งม สเทอร โอไอโซเมอร แตกต างกะน 2 แบบ C 2 C 2 α-anomer β-anomer
16 C. Structure of Monosaccharides Fischer Projection: น ยมใช ส าหระบ open-chain C C C C C 2 C C C 2
17 arworth Formula: น ยมใช ส าหระบ cyclic C 2 2 C β-d-glucopyranose
18 Intramolecular Cyclization อะลด ไฮด หร อค โตน ท าปฏ ก ร ยากะบแอลกอฮอล ให สารท ม หม ไฮดรอกซ ล แล อะลคอกซ โดย ปฏ ก ร ยาร หว าง R- กะบ aldehyde ให เฮม อ ซ ตะล (emiacetal) R R R' C C R + R R C ปฏ ก ร ยาร หว าง R- กะบ ketone ให เฮม ค ตะล (emiketall) + R R R C R'
19 โมโนแซ คคาไรด ม หม - แล aldehyde หร อ ketone อย ในโมเลก ล จ งสามารถเก ดปฏ ก ร ยาภายในโมเลก ลให เฮม อ ซ ตะลหร อเฮม ค ตะลท ม โครงสร างเป นวง : 1 C
20 โมโนแซ คคาไรด จ เก ดเป นวงท ม ออกซ เจนในวง วง 5 เหล ยม (5-membered ring) คล ายฟ วแรน (furan) วง 6 เหล ยม (6-membered ring) คล ายไพแรน (pyran) โมโนแซ คคาไรด ท เก ดเป นวง 5 เหล ยม เร ยกว า furanose โมโนแซ คคาไรด ท เก ดเป นวง 6 เหล ยม เร ยกว า pyranose
21 การเข ยนโครงสร างแบบ aworth projection เปล ยนโครงสร างแบบ Fischer projection เป นแบบ arworth projection ขะ นท 1: 1: จาก Fischer projection ให หม นโมเลก ลตามเข มนาฬ กา ดะงนะ น หม ท อย ทางซ ายม อจ เข ยนในท ศช ลง ส วนหม ท อย ทางขวาม อ จ เข ยนในท ศช ข น C - 2 C C C 2 -
22 ขะ นท 2: 2: เข ยนโครงสร างให เป นวง 6 เหล ยม ให หม -C 22 อย เหน อร นาบของวงแหวนเสมอ (เพรา เป น D-sugar) หม - เข ยนไว ใกล กะบหม -C= - 2 C C C 2 C
23 ขะ นท 3: 3: เข ยนโครงสร างแบบวง ม การสร างพะนธ ร หว าง ของหม - กะบ -C= ได โครงสร างแบบวง เร ยกว า aworth projection C 2 C C 2
24 ขะ นท 4: 4: จากโครงสร างแบบวง พบว า C 11 จะดเป นไคระลคาร บอนตะวใหม ม ม 2 ไอโซเมอร เร ยกว า anomers สามารถเข ยนโครงสร างได 2 แบบ ค อ C 2 1 C 2 1 α-anomer β-anomer
25 แสดงการเก ดโครงสร างแบบวงของ D-glucose C 2 C C C 2 C 2 C 2 C 2 α-d-glucopyranose β-d-glucopyranose
26 แสดงการเก ดโครงสร างแบบวงของ D-glucose C 2 C C C 2 C 2 C 2 C 2 α-d-glucofuranose β-d-glucofuranose
27 แสดงการเก ดโครงสร างแบบวงของ D-fructose C 2 C 2 C C C 2 C 2 C 2 C 2 C 2 α-d-fructopyranose β-d-fructofuranose
28 แสดงการเก ดโครงสร างแบบวงของ D-fructose C 2 C C 2 C 2 2 C C C 2 C 2 C 2 C 2 C 2 C 2 α-d-fructofuranose β-d-fructofuranose
29 ม วตาโรเตชะน (Mutarotation Mutarotation) ปรากฎการณ การเปล ยนแปลงค า specific rotation [α], ของคาร โบไฮเดรท ซ งเป นผลเน องมาจากการเก ดสมด ลของ anomer การเปล ยนแปลงเก ดจากปฏ ก ร ยาผะนกละบของ anomer ซ งแต ล anomer ม ค า [α] ไม เท ากะน สารล ลาย α -D-glucopyranose (m.p 146 o C) วะดค าได [α] (เร มต น) = 112 แล [α] (สมด ล) = 52.7 สารล ลาย β -D-glucopyranose (m.p 150 o C) วะดค าได [α] (เร มต น) = 19 แล [α] (สมด ล) = 52.7
30 C 2 C 2 C 2 α-d-glucopyranose [α] = % ค าท สภาว สมด ล [α] = % β-d-glucopyranose [α] = 19 64%
31 ปฏ ก ร ยาของมอโนแซ ค แซ คคา คาไรด
32 C 2 C 2 open-chain form ม หม aldehyde อ สร ถ ก oxidized ให aldonic acid ใช oxidizing agent ท อ อน เช น Tollens, Fehling แล Benedicts reagent น าตาลร ด วซ (reducing sugar)
33 C 2 C C α-d-glucose C 2 C 2 open-chain Ag(N 3 ) C 2 D-Gluconic acid β-d-glucose
34 Ketone ไม ท าปฏ ก ร ยากะบ oxidizing agent ท อ อน แต ketose เป น reducing sugar เพรา ketose อย ในสมด ลกะบ aldose โดยเก ด tautomerise ผ าน enediol แล ว aldose ถ ก oxidized C 2 C - C 2 C C C R R R Ketose Enediol Aldose
35 ถ า oxidize aldose ด วย oxidizing agent ท แรง เช น dil. N 3 ทะ ง aldehyde แล alcohol ถ ก oxidized ให carboxylic acid เร ยกว า aldraic acid C N 3 C C 2 D-Glucose C D-Glucaric acid
36 หม carbonyl ของ aldose หร อ ketose ถ กร ด วซ ให altidols ใช catalytic hydrogenation หร อ NaB 4 2 C C 2 /Pt or NaB 4 C 2 D-Glucose (cyclic) C 2 D-Glucose (acyclic) C 2 D-Glucitol (sorbital)
37 หม hydroxyl ของ aldose หร อ ketose ท าปฏ ก ร ยากะบ carboxylic acid หร อ anhydride ให ester C 2 β-d-glucose 3 CC CC 3 Pyridine, 0 o C Ac C 2 Ac Ac Ac Ac β-d-glucopyranose pentaacetate
38 emiacetal ท าปฏ ก ร ยากะบ alcohol ให acetal Acetal ของ carbohydrate เร ยกว า glycoside พะนธ ร หว าง anomeric carbon กะบหม -R เร ยกว า glycoside bond หร อ glycosidic linkage C 2 + C 3 + C 2 Glycoside bond C 3 β-d-glucopyranose Methyl-β-D-Glucopyranoside
39 ligosaccharides ท พบมากค อ disaccharides ปร กอบด วย 2 monosaccharide ท เช อมกะนด วย glycoside bond (พะนธ ร หว าง anomeric C กะบ ) Sucrose Lactose Maltose Cellobiose
40 ปร กอบด วย D-glucose แล D-fructose C 2 C 2 C 2 D-fructose จ อย ในร ป furanose เช อมกะนด วย Glycoside bond เป นแบบ 1,2 -α,β link
41 1,2 -α,β link C 2 C C 2 C 2 2 1C 2 C 2 1 = C ต าแหน งท 1 (anomeric C) ของ D-glucose หม - ช ลง (α) 2 = C ต าแหน งท 2 (anomeric C) ของ D-fructose หม - ช ข น (β)
42 C 2 C 2 C 2 ไม ม anomeric C จ งไม เก ด meutarotation เม อล ลายน า ไม ถ ก oxidized ด วย Tollens, Fehling แล Benedict reagent Non-reducing sugar
43 ปร กอบด วย D-glucose 2 หน วย C 2 C 2 เช อมกะนด วย Glycoside bond เป นแบบ 1,4 -α link
44 C 2 C 2 + C C ,4 -α link
45 C 2 C 2 free anomeric C เก ด meutarotation เม อล ลายน า ถ ก oxidized ด วย Tollens, Fehling แล Benedict reagent reducing sugar
46 ปร กอบด วย D-glucose แล D-galactose C 2 C 2 เช อมกะนด วย Glycoside bond เป นแบบ 1,4 -β link
47 C 2 C 2 + C 2 C ,4 -α link + 2
48 C 2 C 2 free anomeric C เก ด meutarotation เม อล ลายน า ถ ก oxidized ด วย Tollens, Fehling แล Benedict reagent reducing sugar
49 ปร กอบด วย D-glucose 2 หน วย C 2 เช อมกะนด วย Glycoside bond เป นแบบ 1,4 -β link
50 C 2 C 2 + C 2 C ,4 -β link
51 C 2 C 2 free anomeric C เก ด meutarotation เม อล ลายน า ถ ก oxidized ด วย Tollens, Fehling แล Benedict reagent reducing sugar
52 Polysaccharides เป น polymer ท ปร กอบด วย monosaccharide จ านวนมากเช อมกะนด วย glycoside bond ส วนใหญ ปร กอบด วย monosac. ชน ดเด ยว Starch Glycogen Cellulose
53 ปร กอบด วย glucose ท เช อมกะนด วย glycoside bond แบบ 1,4 -α link เป นส วนใหญ amylose amylopectin straight chain branched structure น าแป งมาท า partial hydrolysis จ ได maltose ซ งเม อ hydrolysis สมบ รณ จ ได D-glucose
54 Amylose ม อย ปร มาณ 20 % ของแป ง ปร กอบด วย glucose หน วย เช อมกะนด วย 1,4 -α link ไม ล ลายในน าเย น C C C C 2
55 Amylopectin ม อย ปร มาณ 80 % ของแป ง ปร กอบด วย glucose หน วย เช อมกะนด วย 1,4 -α link ม ก งเก ดข นท ก หน วย เช อมแบบ 1,6 -α link ล ลายได ในน าเย น
56 4 4 C 2 1 C C C C 2
57 ปร กอบด วย glucose ท เช อมกะนด วย glycoside bond แบบ 1,4 -α link แล 1,6 -α link คล าย amylopectin แต ม ก งมากกว า โดยม ก งท ก 8-12 หน วย ส สมในเซลล ของสะตว พบมากท ตะบแล กล ามเน อ MW ส งกว าแป ง (100,000 หน วย)
58 ปร กอบด วย glucose (10,000-15,000 หน วย) ท เช อมกะนด วย glycoside bond แบบ 1,4 -β link โดยไม ม ก ง เป น polysaccharide ท พบมากท ส ด เป นส วนแล ปร กอบในพ ช 1 C C 2 4 C C 2 1
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