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1) hydrocarbon non polar 2) acidic 3) basic 4) polar, not charged |
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How to prep an amino acid |
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1) Protein and water takes 7 years
2) protein + 6NHCl, 12hrs, 100degreesC
3) bromination to a CA then amination (won't work on kerosene) 1) Br2 Pbr3 2)H2O then NH4OH
4) from a alpha CA NH3 then 1)NaBH4 2)H2O
5) from a malonate 1) alpha halogenate malonate 2) Gabriel amine synthesis 3) alpha-alkylation 4) hydrolysis/decarboxylation
6)strecker synthesis 1) aldehyde + NH3 + CN- 2) H3O+ |
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1) CA + SOCl2 2) 2 eq. RNH2 OR 1 eq. RNH2 1 eq. ET3N
each AA has nuc and elec so you block reactivity, protect the amine group (nuc) and protect the carbonyl (elec), then the other ends will react, ET3N, then deprotect |
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For CA: Ph-CH2-OH and acid, go back neutrally with H2 Pd/C or acidic with H+
For CA: Bn
For Amine: t-Boc, has a carbonyl group next to it to ensure that N's lone pairs are not active, break with TFA
For Amine: Ac2O, Et3N |
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How do you cleave methionine? |
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cleave after lys (k) and arg (r) |
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what will chymotripsin do? |
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cleave after F, Y, W, anything aromatic |
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How to make the OH on the CA a better leaving group? |
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Method 1: SOCl2 Method 2: DCC |
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90%= dipeptide (.9)^2 =tripeptide (.9)^49=50mer |
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Edman, Cyanogen Bromide, enzymes, bN HCl thing |
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with 100degrees changes protein to amino acid
can change the NH2 by a carbonyl to OH and the NH2 free standing to NH3+ |
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Kinetic vs Thermodynamic product? |
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S in ring is kinetic while N is thermodynamic because of the valence electrons of N are closer to the nucleus, tighter and strong bond made |
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