SYNTHESIS OF GLYCURONAMIDES OF AMINO-ACIDS, CONSTITUENTS OF MICROBIAL POLYSACCHARIDES AND THEIR CONVERSION INTO NEOGLYCOCONJUGATES OF COPOLYMER TYPE

被引:20
作者
CHERNYAK, AY [1 ]
SHARMA, GVM [1 ]
KONONOV, LO [1 ]
KRISHNA, PR [1 ]
RAO, AVR [1 ]
KOCHETKOV, NK [1 ]
机构
[1] INDIAN INST CHEM TECHNOL,HYDERABAD 500007,INDIA
关键词
AMINO ACID-GLYCURONAMIDES; SYNTHESIS; NEOGLYCOCONJUGATES;
D O I
10.1007/BF00731016
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Glycopyranosiduronic acids, amidically linked to amino acids (alanine, serine, threonine, and lysine) were prepared. O-tert-Butyl and N-epsilon-tert-butyloxycarbonyl protected amino acid tert-butyl esters were used in ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate promoted condensation with 2-azidoethyl glycosides of glucuronic and galacturonic acid. Reduction of the azido-function followed by N-acryloylation and removal of blocking groups with trifluoroacetic acid gave the target monomers. These were converted into neoglycoconjugates of copolymer type, potentially useful for immunochemical studies.
引用
收藏
页码:82 / 89
页数:8
相关论文
共 27 条
[1]   PREPARATION, PROPERTIES, AND APPLICATIONS OF CARBOHYDRATE CONJUGATES OF PROTEINS AND LIPIDS [J].
APLIN, JD ;
WRISTON, JC .
CRC CRITICAL REVIEWS IN BIOCHEMISTRY, 1981, 10 (04) :259-306
[2]   A NEW CONVENIENT REAGENT FOR PEPTIDE SYNTHESES [J].
BELLEAU, B ;
MALEK, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (06) :1651-&
[3]   SYNTHESIS OF 1,2-O-CYANOETHYLIDENE DERIVATIVES OF ALKYL GLYCOPYRANURONATES BY OXIDATION OF THE 6-TRITYL ETHERS OF THEIR HEXOSE ANALOGS [J].
BETANELI, VI ;
OTT, AY ;
BRUKHANOVA, OV ;
KOCHETKOV, NK .
CARBOHYDRATE RESEARCH, 1988, 179 :37-50
[4]  
BOVIN NV, 1985, BIOORG KHIM+, V11, P662
[5]   RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].
BOWDEN, K ;
HEILBRON, IM ;
JONES, ERH ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45
[6]   STRUCTURAL STUDIES OF THE CAPSULAR POLYSACCHARIDE ELABORATED BY HEMOPHILUS-INFLUENZAE TYPE-D [J].
BRANEFORSHELANDER, P ;
KENNE, L ;
LINDBERG, B ;
PETERSSON, K ;
UNGER, P .
CARBOHYDRATE RESEARCH, 1981, 97 (02) :285-291
[7]  
CHERNYAK AY, 1989, BIOORG KHIM+, V15, P1394
[8]   PREPARATION OF OLIGOSACCHARIDE-POLYACRYLAMIDE CONJUGATES AND THEIR USE AS ANTIGENS IN ENZYME-IMMUNOASSAY (EIA) [J].
CHERNYAK, AY ;
WEINTRAUB, A ;
NORBERG, T ;
KALLIN, E .
GLYCOCONJUGATE JOURNAL, 1990, 7 (02) :111-119
[9]  
CHERNYAK AY, 1988, BIOORG KHIM+, V14, P1047
[10]   STRUCTURE OF THE SERINE-CONTAINING CAPSULAR POLYSACCHARIDE-K-40 ANTIGEN FROM ESCHERICHIA-COLI O8-K-40-H9 [J].
DENGLER, T ;
JANN, B ;
JANN, K .
CARBOHYDRATE RESEARCH, 1986, 150 (01) :233-240