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Query: CAS:22594-61-2 (KDN)
 87 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The sugar nucleotide, cytidine 5'-(3-deoxy-D-glycero-D-galacto-2-nonulosonic phosphate) (CMP-KDN) is expected to serve as a donor of KDN residues in the synthesis of KDN-containing glycoconjugates. We report here the identification and characterization of CMP-KDN synthetase, a novel enzyme responsible for synthesis of CMP-KDN from KDN and CTP. The enzyme was partially purified from the testis of rainbow trout (Oncorhynchus mykiss), where KDN gangliosides were first discovered (Yu, S., Kitajima, K., Inoue, S., and Inoue, Y. (1991) J. Biol. Chem. 266, 21929-21935), and used to synthesize CMP-[14C]KDN, which was characterized by 1H NMR. Vmax/Km studies showed that KDN was a preferred nonulosonic acid substrate compared to N-acetylneuraminic acid (Neu5Ac) or N-glycolylneuraminic acid (Neu5Gc) (4.4 x 10(-3) min-1 for KDN versus 2.3 and 1.8 x 10(-3) min-1 for Neu5Ac and Neu5Gc, respectively). CMP-KDN synthetase activity was maximal at pH 9-10 and at 25 degrees C. The presence of either Mg2+ or Mn2+ was essential for CMP-KDN synthetase activity. 25 mM Mg2+ stimulated formation of CMP-KDN more than 10-fold, yet only stimulated formation of CMP-Neu5Ac and CMP-Neu5Gc 4-fold, relative to 1 mM Mg2+. A kinetic study using mixed substrates showed that both CMP-KDN and CMP-Neu5Ac synthetase activities in the partially purified enzyme were due to the same active site of a single enzyme. In contrast, Neu5Ac and Neu5Gc were the preferred nonulosonic acid substrates for the calf brain CMP-sialic acid synthetase. Thus, mammalian CMP-sialic acid synthetases recognizes similar, yet distinctively different, substrate specificity determinants. Thus, the trout testis enzyme was considered to synthesize activated sugar nucleotides required for synthesis of both (KDN)GM3 and (Neu5Ac)GM3. The expression of CMP-KDN synthetase was shown to be temporally correlated with development and to parallel the developmental expression of (KDN)GM3 in sperm.
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PMID:Synthesis of CMP-deaminoneuraminic acid (CMP-KDN) using the CTP:CMP-3-deoxynonulosonate cytidylyltransferase from rainbow trout testis. Identification and characterization of a CMP-KDN synthetase. 838 11

[reaction: see text] beta-D-Galp-(1-->9)-D-KDN, a disaccharide component of the cell wall of Streptomyces sp. MB-8, was synthesized from beta-D-Galp-(1-->6)-D-Manp and pyruvate using a sialic acid aldolase. The obtained KDN-containing compound was a novel acceptor for bacterial sialyltransferases. Unusual alpha2,3- and alpha2,6-linked sialyltrisaccharides and a tetrasaccharide were synthesized using a one-pot two-enzyme system containing a Neisseria meningitidis CMP-sialic acid synthetase and a Pasteurella multocida sialyltransferase or a Photobacterium damsela alpha2,6-sialyltransferase.
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PMID:Aldolase-catalyzed synthesis of beta-D-galp-(1-->9)-D-KDN: a novel acceptor for sialyltransferases. 1670 34