Biomaterial Database

Synthesis of sialic acid-containing nucleotide sugars: CMP-sialic acid analogs. 1992

K Ikeda, and Y Nagao, and K Achiwa

School of Pharmaceutical Sciences, University of Shizuoka, Japan.

Syntheses of some sialic acid-containing nucleotide sugars are reported. The reaction of methyl [(2-hydroxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosid]onate (4) with various fully protected hydrogen phosphonates of nucleosides (5a-c) in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride (TPSCl), gave, after oxidation and deprotection, the corresponding sialic acid-containing nucleotide sugar analogs (8a-c).

UI	MeSH Term	Description	Entries
D003568	Cytidine Monophosphate	Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.	CMP,Cytidylic Acid,2'-CMP,3'-CMP,Cytidylic Acids,2' CMP,3' CMP,Acid, Cytidylic,Acids, Cytidylic,Monophosphate, Cytidine
D000216	N-Acylneuraminate Cytidylyltransferase	An enzyme that forms CMP-acylneuraminic acids, which donate the N-acylneuraminic acid residues to the terminal sugar residue of a ganglioside or glycoprotein. EC 2.7.7.43.	Acylneuraminate Cytidylyltransferase,CMP Sialate Pyrophosphorylase,CMP Sialate Synthase,CMP-N-Acetylneuraminic Acid Synthetase,CMP-Sialic Acid Synthetase,Cytidine 5'-Monophosphosialic Acid Synthetase,Cytidine 5-Monophosphosialate Synthase,CMP N Acetylneuraminic Acid Synthetase,CMP Sialic Acid Synthetase,Cytidine 5 Monophosphosialate Synthase,Cytidine 5' Monophosphosialic Acid Synthetase,Cytidylyltransferase, Acylneuraminate,Cytidylyltransferase, N-Acylneuraminate,N Acylneuraminate Cytidylyltransferase,Pyrophosphorylase, CMP Sialate,Sialate Pyrophosphorylase, CMP,Sialate Synthase, CMP,Synthase, CMP Sialate,Synthase, Cytidine 5-Monophosphosialate,Synthetase, CMP-N-Acetylneuraminic Acid,Synthetase, CMP-Sialic Acid
D000998	Antiviral Agents	Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.	Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D012794	Sialic Acids	A group of naturally occurring N-and O-acyl derivatives of the deoxyamino sugar neuraminic acid. They are ubiquitously distributed in many tissues.	N-Acetylneuraminic Acids,Acids, N-Acetylneuraminic,Acids, Sialic,N Acetylneuraminic Acids
D012799	Sialyltransferases	A group of enzymes with the general activity CMP-N-acetylneuraminate:acceptor N-acetylneuraminyl transferase. They catalyze the transfer of N-ACETYLNEURAMINIC ACID from CMP-N-ACETYLNEURAMINIC ACID to an acceptor, which is usually the terminal sugar residue of an oligosaccharide, a glycoprotein, or a glycolipid.	Glycoprotein Sialyltransferases,Glycosyltransferase Family 29,Sialyltransferase,Ectosialyltransferase,Glycoprotein Sialyltransferase,Sialyltransferase, Glycoprotein,Sialyltransferases, Glycoprotein
D013938	Thymidine Monophosphate	5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.	DTMP,TMP,Thymidylic Acid,Deoxythymidylate,Thymidylic Acids,Acid, Thymidylic,Acids, Thymidylic,Monophosphate, Thymidine
D013942	Thymine Nucleotides	Phosphate esters of THYMIDINE in N-glycosidic linkage with ribose or deoxyribose, as occurs in nucleic acids. (From Dorland, 28th ed, p1154)	Thymidine Phosphates,Nucleotides, Thymine,Phosphates, Thymidine
D015215	Zidovudine	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.	AZT (Antiviral),Azidothymidine,3'-Azido-2',3'-Dideoxythymidine,3'-Azido-3'-deoxythymidine,AZT Antiviral,AZT, Antiviral,BW A509U,BWA-509U,Retrovir,3' Azido 2',3' Dideoxythymidine,3' Azido 3' deoxythymidine,Antiviral AZT,BWA 509U,BWA509U
D054306	Dideoxynucleotides	The phosphate esters of DIDEOXYNUCLEOSIDES.	Dideoxynucleotide Triphosphates,ddNTPs,Triphosphates, Dideoxynucleotide
D019158	N-Acetylneuraminic Acid	An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518)	Sialic Acid,Acid, N-Acetylneuraminic,Acid, Sialic,N Acetylneuraminic Acid