Peptides & PLP - Lecture Notes | Lecture Note - Edubirdie

University:
York University
Course:
CHEM 2021 | Introductory Organic Chemistry II
Academic year:

2023
Views:

283

Pages:

3
Author:

Niklas

Peptides & PLP Peptide Example: N-terminus C-terminus H3N+ O | || H2N-CH-C-NH-CH-C-NH-CH-C-OH | || CH3 Ph 3-Letter Notation: H₃N-Ala-Val-Phe-OH 1-Letter Notation: H₃N-A-V-F-OH Peptide Bonds → Amide Bonds R R || || C-N-C-R' || || R' How to Make Amide Bond? From acyl chloride: Ph-C=O + H2N-R → Ph-C-NH-R Cl O From acid anhydride: Bu-C=O + H2N-R → Bu-C-NH-R O=C-Bu O From carboxylic acid: Ph-C-OH + H2N-R → NO RXN (acid-base rxn) O Coupling reagent: DCC ("dicyclohexylcarbodiimide") N=C=N Cy-N=C=N-Cy Coupling reagent: EDC ("1-ethyl-3-(3-dimethylaminopropyl) carbodiimide") N=C=N Forming Amide Bond: CH3 Me Me || || || NH3+ - C - COO- + NH3+ - C - COO- + NH3+ - C - COO- + NH3+ - C - COO- || || || Ph Ph Ph DCC DCM Me Me || || Ph - C - NH - C - COO- + NH3+ - C - COO- || || Ph Ph 4 possible products... Need a P! → NH₂ protecting groups Protecting Groups: t-BuO-C-N-R || O t-Butoxycarbonyl (Boc): Acidic cond. (H+) Ph-C-N-R || O Carbobenzyloxy (Cbz): Neutral cond.

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