Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain.
Among many hurdles in synthesizing proteoglycan glycopeptides, one challenge is the incorporation of aspartic acid in the peptide backbone and acid sensitive O-sulfated glycan chains. To overcome this, a new strategy was developed utilizing homoserine as an aspartic acid precursor. The conversion of homoserine to aspartic acid in the glycopeptide was successfully accomplished by late stage oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (TEMPO) and bis(acetoxy)iodobenzene (BAIB). This is the first time that a glycopeptide containing aspartic acid and an O-sulfated glycan was synthesized.
Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Weizhun
W
Yang
Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.|Chemistry Department, Faculty of Science, Benha University , Benha, Qaliobiya 13518, Egypt.
Sherif
S
Ramadan
Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Bo
B
Yang
Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Keisuke
K
Yoshida
Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Xuefei
X
Huang
D001224:Aspartic Acid / Q000737:chemistry*; D002240:Carbohydrate Sequence; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006714:Homoserine / Q000737:chemistry*; D013058:Mass Spectrometry; D011134:Polysaccharides / Q000737:chemistry*; D011509:Proteoglycans / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D060327:Solid-Phase Synthesis Techniques; D013431:Sulfates / Q000737:chemistry
D006020:Glycopeptides; D011134:Polysaccharides; D011509:Proteoglycans; D013431:Sulfates; D001224:Aspartic Acid; D006714:Homoserine