Biomaterial Database

Chemical synthesis of normal and transformed PSA glycopeptides. 2004

Vadim Y Dudkin, and Justin S Miller, and Samuel J Danishefsky

Laboratory for Bioorganic Chemistry, The Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.

Chemical syntheses are reported for prostate specific antigen (PSA) N-linked glycopeptide fragments consisting of an uneicosapeptide (residues 27-47 of PSA) with di-, tri-, and tetrabranched N-acetyllactosamine-type glycans. The syntheses involve simultaneous, multiple glycosylations of the corresponding pentasaccharide acceptors prepared from a common trisaccharide precursor. Globally deprotected glycans are aminated and then aspartylated with a hexapeptide, which is then extended using native chemical ligation (NCL). The glycopeptides will be used for the generation of antibodies that may form the basis for a new prostate cancer diagnostic assay.

UI	MeSH Term	Description	Entries
D008969	Molecular Sequence Data	Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories.	Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
D011134	Polysaccharides	Long chain polymeric CARBOHYDRATES composed of MONOSACCHARIDES linked by glycosidic bonds.	Glycan,Glycans,Polysaccharide
D002240	Carbohydrate Sequence	The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS.	Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D006020	Glycopeptides	Proteins which contain carbohydrate groups attached covalently to the polypeptide chain. The protein moiety is the predominant group with the carbohydrate making up only a small percentage of the total weight.	Glycopeptide
D000595	Amino Acid Sequence	The order of amino acids as they occur in a polypeptide chain. This is referred to as the primary structure of proteins. It is of fundamental importance in determining PROTEIN CONFORMATION.	Protein Structure, Primary,Amino Acid Sequences,Sequence, Amino Acid,Sequences, Amino Acid,Primary Protein Structure,Primary Protein Structures,Protein Structures, Primary,Structure, Primary Protein,Structures, Primary Protein
D000606	Amino Sugars	SUGARS containing an amino group. GLYCOSYLATION of other compounds with these amino sugars results in AMINOGLYCOSIDES.	Amino Sugar,Sugar, Amino,Sugars, Amino
D017430	Prostate-Specific Antigen	A glycoprotein that is a kallikrein-like serine proteinase and an esterase, produced by epithelial cells of both normal and malignant prostate tissue. It is an important marker for the diagnosis of prostate cancer.	Kallikrein hK3,gamma-Seminoprotein,hK3 Kallikrein,Prostate Specific Antigen,Semenogelase,Seminin,Kallikrein, hK3,gamma Seminoprotein