Solution phase synthesis of amide-linked N-acetyl neuraminic acid, alpha-amino acid, and sugar amino acid conjugates

被引:27
作者
Ramamoorthy, PS [1 ]
Gervay, J [1 ]
机构
[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721
关键词
D O I
10.1021/jo9711246
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Peracetylated N-acetylneuraminic acid (NeuAc) was efficiently coupled to esters of glycine, alanine, and serine using BOP and HOBT in the presence of DIEA. Deprotection of the esters readied the NeuAc-alpha-amino acid conjugates for further elaboration. Coupling of the NeuAc-gly adduct with beta-O-methoxy neuraminic acid methyl ester afforded a selectively protected glycine linked sialic acid dimer. 2-Amino-3,4-di-O-benzyl-(1-->6)-anhydroglucose and alanine benzyl ester were also efficiently coupled to the bis adduct giving novel trimeric analogs. Elimination of the anomeric acetate from the NeuAc-gly dimer followed by global deprotection provided a novel saccharopeptide with modest clostridial sialidase inhibitory activity.
引用
收藏
页码:7801 / 7805
页数:5
相关论文
共 50 条
[31]   SYNTHESIS OF N-(JASMONOYL)AMINO ACID CONJUGATES [J].
KRAMELL, R ;
SCHMIDT, J ;
SCHNEIDER, G ;
SEMBDNER, G ;
SCHREIBER, K .
TETRAHEDRON, 1988, 44 (18) :5791-5807
[32]   ALPHA-OXIMINO ACID INTERMEDIATES FOR THE SYNTHESIS OF ALPHA-AMINO ACIDS [J].
BARRY, RH ;
HARTUNG, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1947, 12 (03) :460-468
[33]   SYNTHESIS AND EVALUATION OF THE HYDROLYTICAL STABILITY OF ETHYL 2-(ALPHA-AMINO ACID)GLYCOLATES AND ETHYL 2-(ALPHA-AMINO ACID)LACTATES [J].
CROMMEN, JHL ;
SCHACHT, EH .
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1991, 100 (10) :747-758
[34]   SYNTHESIS OF ALPHA-AMINO ACID MENTHYL ESTERS .2. [J].
HAYAKAWA, T ;
HARADA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1965, 38 (08) :1354-+
[35]   PREPARATION OF DERIVATIVES OF NITROGEN MUSTARD HAVING STRUCTURE OF ALPHA-AMINO ACID AMIDE [J].
SAKURAI, Y ;
MATSUI, E .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1965, 13 (05) :594-+
[36]   POLYMERIZATION OF ALPHA-AMINO ACID N-CARBOXY ANHYDRIDE .9. COPOLYMERIZATION OF ALPHA-AMINO ACID N-CARBOXY ANHYDRIDE IN HETEROGENEOUS SYSTEM [J].
OYA, M ;
UNO, K ;
IWAKURA, Y .
JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1972, 10 (02) :613-&
[37]   N-ACETYL NEURAMINIC-ACID CONTENT OF MILK OF VARIOUS SPECIES [J].
MORRISSEY, PA .
JOURNAL OF DAIRY RESEARCH, 1973, 40 (03) :421-425
[38]   Synthesis and structural characterization of (1→5) amide linked N-acetyl neuaraminic acid derivatives. [J].
Gregar, TQ ;
Gervay, J .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 :U197-U197
[39]   Oxidative Deamination of N-Acetyl Neuraminic Acid: Substituent Effects and Mechanism [J].
Buda, Szymon ;
Crich, David .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (03) :1084-1092
[40]   INHIBITION OF STREPTOCOCCAL AGGLUTINATION CAUSED BY HAPTOGLOBIN BY MEANS OF N-ACETYL NEURAMINIC ACID (SIALINIC ACID) [J].
MONTAG, T .
DEUTSCHE GESUNDHEITSWESEN-ZEITSCHRIFT FUR KLINISCHE MEDIZIN, 1979, 34 (45) :2266-2267