Synthesis of CMP-9″-modified-sialic acids as donor substrate analogues for mammalian and bacterial sialyltransferases

Carbohydrate Research

Volumn 342, Issue 12-13, 2007, Pages 1680-1688

  Kajihara, Yasuhiro ^a   Kamitani, Toshimi ^a   Sato, Reiko ^a   Kamei, Naoki ^b   Miyazaki, Tatsuo ^a   Okamoto, Ryo ^a   Sakakibara, Thoru ^a   Tsuji, Takashi ^b   Yamamoto, Takeshi ^c  

^a YOKOHAMA CITY UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c JAPAN TOBACCO INC   (Japan)

Author keywords

CMP Neu5Ac; Enzymatic synthesis; Sialyltransferase

Indexed keywords

ALKYLCARBOXYLIC ACID DERIVATIVES; CMP-NEU5AC; ENZYMATIC SYNTHESIS; SIALYLTRANSFERASE;

AMIDES; CARBOXYLIC ACIDS; DERIVATIVES; ENZYME ACTIVITY; NUCLEOTIDES; SUBSTRATES; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

2 CYANOETHYL 2',3' O N4, TRIACETYLCYTIDINE 5' YL N,N DIISOPROPYLPHOSPHORAMIDITE; ALKYL GROUP; AMIDE; AZIDE; BACTERIAL ENZYME; CARBOXYLIC ACID; CYTIDINE 5' MONOPHOSPHO SIALIC ACID; METHYL 5 ACETAMIDO 4,7,8 TRI O ACETYL 9 AZIDO 3,5,9 TRIDEOXY BETA DEXTRO GLYCERO DEXTRO GALACTO 2 NONULOPYRANOSONATE; PHENYL GROUP; PHOSPHITE; PHOSPHORAMIDIC ACID DERIVATIVE; PYRANOSIDE; SIALIC ACID DERIVATIVE; SIALYLTRANSFERASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME ASSAY; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; MAMMAL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; RAT; REDUCTION;

ANIMALS; BACTERIA; BACTERIAL PROTEINS; CYTIDINE MONOPHOSPHATE N-ACETYLNEURAMINIC ACID; ENZYME INHIBITORS; MAMMALS; MODELS, MOLECULAR; SIALYLTRANSFERASES; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS); MAMMALIA; PHOTOBACTERIUM; RATTUS;

EID: 34447310551     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2007.05.029     Document Type: Article

References (17)

1. Mirelis P., and Brossmer R. Bioorg. Med. Chem. Lett. 5 (1995) 2809-2814
2. Kosa R.E., Brossmer R., and Gross H.J. Biochem. Biophys. Res. Commun. 190 (1993) 914-920
3. Gross H.J., Rose U., Krause J.M., Paulson J.C., Schmid K., Feeny R.E., and Brossmer R. Biochemistry 28 (1989) 7386-7392
4. Gross H.J., and Brossmer R. Euro. J. Biochem. 177 (1988) 583-589
5. Gross H.J., Buensch A., Paulson J.C., and Brossmer R. Euro. J. Biochem. 168 (1987) 595-602
6. Gross H.J., and Brossmer R. Glycoconjugate J. 4 (1987) 145-156
7. Kajihara Y., Ebata T., and Kodama H. Angew. Chem., Int. Ed. 37 (1998) 3166-3169
8. Chiu C.P.C., Watts A.G., Lairson L.L., Gilbert M., Lim D., Wakarchuk W.W., Withers S.G., and Strynadka N.C.J. Nat. Struct. Mol. Biol. 11 (2004) 163-170
9. Ni L., Sun M., Yu H., Chokhawala H., Chen X., and Fisher A.J. Biochemistry 45 (2006) 2139-2148
10. Yu H., Chokhawala H., Karpel R., Yu H., Wu B., Zhang J., Zhang Y., Jia Q., and Chen X. J. Am. Chem. Soc. 127 (2005) 17618-17619
11. Yu H., Huang S., Chokhawala H., Sun M., Zheng H., and Chen X. Angew. Chem., Int. Ed. 45 (2006) 3938-3944
12. Kajihara Y., Yamamoto T., Nagae H., Nakashizuka M., Sakakibara T., and Terada I. J. Org. Chem. 61 (1996) 8632-8635
13. Kajihara Y., Ebata T., Koseki K., Kodama H., Matsushita H., and Hashimoto H. J. Org. Chem. 60 (1995) 5732-5735
14. Kajihara Y., Kamitani T., and Sakakibara T. Carbohydr. Res. 331 (2001) 455-459
15. Yem A.W., Zurcher-Neely H.A., Richard K.A., Staite N.D., Heinrikson R.L., and Deibel Jr. M.R. J. Biol. Chem. 264 (1989) 17691-17697
16. Haellgren C., and Hindsgaul O. J. Carbohydr. Chem. 14 (1995) 453-464
17. Yamamoto T., Nakashizuka M., Kodama H., Kajihara Y., and Terada I. J. Biolchem. 120 (1996) 104-110