310-28-1 - CH 310 N T Th 2-3:30 LECTURE 28 Textbook...

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CH 310 N T Th 2-3:30 LECTURE 28 Textbook Assignment: Chapter 26 (selections) Homework (for credit): POW 13 posted Today’s Topics: AA’s & Proteins (finish course) Notice & Announcements: FINAL EXAM IN THIS CLASS IS Saturday, December 12, 7:00–10:00 pm Last Name A-L in WEL:1.308; M-Z WEL: 1.316 Organic Lecture Series 2 Amino Acids Amino Acids and and Proteins Proteins
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Organic Lecture Series NH 3 + CO 2 - Organic Lecture Series 4 Amino Acids Amino Acids • Amino acid: Amino acid: a compound that contains both an amino group and a carboxyl group α -Amino acid: Amino acid: an amino acid in which the amino group is on the carbon adjacent to the carboxyl group – although α -amino acids are commonly written in the unionized form, they are more properly written in the zwitterion zwitterion (internal salt) form RCHCOH NH 2 O RCHCO - 3 + O
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Organic Lecture Series 5 In 1891, Emil Fischer made the arbitrary assignments of D- and L- to the enantiomers of glyceraldehyde (aldehyde is C1-at the top). CHO HO H CH 2 OH 2 H DD L-Glyceraldehyde D-Glyceraldehyde [ α ] 25 = +13.5 [ α ] 25 = -13.5 -OH to Right -OH to Left D,L D,L Monosaccharides Monosaccharides Organic Lecture Series 6 Chirality of Amino Acids Chirality of Amino Acids • With the exception of glycine, all protein- derived amino acids have at least one stereocenter ( the α -carbon ) and are chiral – the vast majority have the L-configuration at their α -carbon COO - 3 H H 3 N L-Alanine - 3 HN H 3 + D-Alanine
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Organic Lecture Series 7 Nonpolar side chains Nonpolar side chains NH 3 + COO - 3 + COO - 3 + COO - 3 + COO - 3 + COO - S 3 + COO - N HH COO - 3 + COO - N H COO - 3 + Alanine (Ala, A) Glycine (Gly, G) Isoleucine (Ile, I) Leucine (Leu, L) Methionine (Met, M) Phenylalanine (Phe, F) Proline (Pro, P) Tryptophan (Trp, W) Valine (Val, V) Organic Lecture Series 8 N COO - Proline (Pro, P) Captopril- ACE Inhibitor Angiotensin Converting Enzyme Angiotensin I Angiotensin II Angiotensin II is a potent vasoconstrictor so, ACE inhibitors are used for the treatment of hypertension
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Organic Lecture Series 9 Polar side chains Polar side chains NH 3 + COO - H 2 N O 3 + - H 2 N O 3 + - HO 3 + - OH Asparagine (Asn, N) Glutamine (Gln, Q) Serine (Ser, S) Threonine (Thr, T) Amide Side Chains Hydroxyl Side Chains Organic Lecture Series 10 Acidic & Basic Side Chains Acidic & Basic Side Chains 3 + - - O O 3 + - - O O 3 + - HS 3 + - 3 + - N H H 2 N 2 + 3 + - N N H 3 + - H 3 N Cysteine (Cys, C) Tyrosine (Tyr, Y) Glutamic acid (Glu, E) Aspartic acid (Asp, D) Histidine (His, H) Lysine (Lys, K) Arginine (Arg, R) +
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Organic Lecture Series 11 NH 3 + COO - N H H 2 N O 3 + COO - H 3 N HO O CH 2 CHCOO - 3 + II I I 3 + - O O L-Citrulline L-Ornithine L-Thyroxine, T 4 4-Aminobutanoic acid ( γ -Aminobutyric acid, GABA) + Other Amino Acids Other Amino Acids Organic Lecture Series 12 Acid Acid -Base Properties Base Properties p K a of p K a valine 2.29 9.72 tryptophan 2.38 9.39 9.10 2.09 threonine serine 2.21 9.15 10.60 2.00 proline phenylalanine 2.58 9.24 9.21 2.28 methionine 9.74 2.33 leucine isoleucine 2.32 9.76 glycine 2.35 9.78 9.13 2.17 glutamine 8.80 2.02 asparagine 9.87 2.35 alanine Nonpolar & polar side chains α− 3 + COOH
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Organic Lecture Series 13 Acid Acid - - Base Properties Base Properties p K a of p K a p K a 10.07 9.11 2.20 tyrosine lysine 2.18 8.95 10.53 6.10 9.18 1.77 histidine glutamic acid 2.10 9.47 4.07 8.00 10.25
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This note was uploaded on 03/16/2010 for the course CH 53705 taught by Professor Colapret during the Fall '09 term at University of Texas at Austin.

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310-28-1 - CH 310 N T Th 2-3:30 LECTURE 28 Textbook...

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