Question

Question #1 (Total: 40% N-Acetylglucosamine is commonly known as an amide derivative of the monosaccharide glucose with the following structure: ОН HOO OH NH O= CH3 You are told that the B1 group of N-Acetylglucosamine is chemically linked to a side-chain of the following peptide (through a "glucosidic-like" bond): Phe-Gly-Ser-Ala НО Please propose a mechanism in the coupling between N-Acetylglucosamine and Phe-Gly- Ser-Ala. [15 points] Please clearly show the linkage between N-Acetylglucosamine and Phe-Gly-Ser-Ala in a detailed diagram. [25 points]

Answer 1

Mechanizm NAely lgluco но SA Mie NH2 HO HOOC-CINY CM2 11 HOOC-CH HOOC-C-NH, H.A-CIH CM2-Ph CW3 PhesPhe ngk alanne Caly-glycine Ala Ser R-OH Serne Alanime RHO RI-don Gly-Ser- Ah CH I C2-Ph R-öH fhe- Step- Used H tH froton exchange elimination R-O -H20 IH Step-II Yelease НО -R -froduct linkage NHZ HO H -CH C-CH2 -CH CICHIN NH 1 CH2 HO Ch3 Ald CH2 ch3 G1y NAG N-Acely ghicasamdno Sex phe