- I M Working On The Synthesis And Identification Of A Dipeptide Lab And Trying To Decode My Carbon And Proton Nmrs To B 1 (187.8 KiB) Viewed 40 times
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- I M Working On The Synthesis And Identification Of A Dipeptide Lab And Trying To Decode My Carbon And Proton Nmrs To B 6 (91.76 KiB) Viewed 40 times
Synthesis and Identification of a Dipeptide клон на осно + OH OCH 3 R R' BocHN. R O-H BocHN BocHN. RH EDCI-HCI = R Et₂N BocHN LOCH 3 ΘΗ Boc t-butoxycarbonyl = Required Reading: Klein Ch 25.1, 25.2, and 25.6 Purpose: You and a partner will synthesize an unknown dipeptide using peptide bond forming reagent EDCI.HC1, 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride. You will be assigned two amino acids, one a Boc-protected amino acid where the R side chain can be one of twenty possibilities, and an amino acid methyl ester hydrochloride where the R' side chain can once again be one of twenty possibilities. Se R + Et3NH BocHN. 1-ethyl-3-(3'-dimethylaminopropyl) _ carbodiimide hydrochloride Using the base triethylamine and the peptide coupling agent EDCI.HCl, you will couple these two amino acids together making a dipeptide. The mechanism for the reaction is given below. EDCI-HCI Et₂ N BocHN. O R' ㅛ I N R H O OCH 3 CO R' RHHO your BocHN -NH LOCH3 BocHN. \ⓇH R -NH N=C=N O R H To -N-H BocHN. H₂N R 0 CI R' LOCH3 ? R' O ΝΗ OCH3 OCH 3 N CIH The Boc group is used to protect amines and is very commonly utilized in peptide syntheses. EDCI HCl, despite the mechanism's apparent complexity, only serves to activate the acid's carbonyl carbon to nucleophili attack by the free amine of the methyl ester. Given the many combinations of side chains, there are many possible dipeptides. You will isolate and purify your dipeptide and determine its structure via IR, ¹H NMR, ¹3C NMR, and
X: parts per Million: 13C 171.785 171.499 155.713 135.797- 129.368 129.263 128.567 127.098 79.798 77.404 77.146 76.888 65.843 59.147 53.176 52.280 37.915 37.219 28.310 24.628 V 15.376 15.252 11.351 111 T T 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 abundance 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2
X:parts per Million: 1H 0.865 人 YYY 7.0 6.0 5.0 4.0 3.0 2.0 1.0 abundance 1.0 0.98 1.00 - 2.0 0.88 0.81 1.37 1.42 1.29 3.0 4.67 5.0 6.0 7.07 7.0 8.0 9.0 10.0 14.07 11.0
X: parts per Million : 1H د نیا نیا نیا دی دی ARK YW 7.0 6.0 5.0 4.0 3.0 abundance 0 1.0 2.0 0.98 0.88 L 0.81 3.0 4.0 5.0 6.0 7.0 4.67 8.0 9.0 10.0 11.0
abundance 11.0 10.0 9.0 8.0 6.0 5.0 4.0 3.0 2.0 1.0 2.7 2.6 2.5 X: parts per Million : 1H 1.23 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.458 1.441 14.07 1.204 N 1.217 1.190 1.4 1.3 1.2 1.1 1.0 0.9 0.8 0.898 0.886 0.873 0.865 0.7 0.6
H H₂N-C-C H Glycine (Gly/G) H H₂N-C-C I CH₂ I CH CH₂ CH₂ =0 Leucine (Leu/L) H I H₂N-C-C CH₂ I OH Serine (Ser / S) =0 H 1 H₂N-C-C CH, Alanine (Ala/A) H H₂N-C-C H₂C-CH I CH₂ I CH, Isoleucine (lle /1) H 1 H₂N-C-C CH OH CH₂ =0 Threonine (Thr/T) NON-POLAR H H₂N-C-C CH / CH, CH₂ Valine (Val/V) H 1 H₂N-C-C T CH₂ CH₂ I S I CH₂ 0 =0 Methionine (Met / M) H H₂N-C-C CH₂ POLAR =0 OH Tyrosine (Tyr/Y) H H₂N-C-C CH₂ SH Cysteine (Cys/C) H I H₂N-C- I CH₂ HN Tryptophan (Trp/W) H 1 H₂N-C-C CH₂ G=0 NH₂ 0 =0 0- Asparagine (Asn / N) HICIC H₂N-C-C T H₂C CH₂ CH₂ Proline (Pro/P) H I H₂N-C-C 1. CH₂ H T H₂N-C-C O CH₂ 1 CH₂ = Phenylalanine (Phe/F) O- =0 =0 NH₂ Glutamine (Gln/Q) + CHARGE H H₂N-C-C CH₂ CH₂ CH₂ CH₂ NH₂+ =0 Lysine (Lys / K) H 1 H₂N-C-C H H₂N-C-C. CH₂ H H₂N-C-C =0 Aspartic Acid (Asp/D) NH NH* Histidine (His/H) CH₂ CH₂ CH₂ NH C =NH, NH₂ - CHARGE Arginine (Arg/R) H H₂N-C-C CH₂ I CH₂ Glutamic Acid (Glu/E)