Details
| Original language | English |
|---|---|
| Pages (from-to) | 2075-2082 |
| Number of pages | 8 |
| Journal | Carbohydrate Research |
| Volume | 343 |
| Issue number | 12 |
| Publication status | Published - 10 Feb 2008 |
Abstract
7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with d-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-d-mannosamine. Aldolase catalyzed transformation yielded the corresponding fluorinated sialic acid which was activated as CMP ester using three different synthetases in the presence as well as in the absence of pyrophosphatase which possesses inhibitory properties. Finally, conditions were optimized to perform a one-pot reaction starting from fluorinated mannosamine, which yielded the 7-fluoro-7-deoxy-CMP-sialic acid by incubation with three enzymes.
Keywords
- Chemoenzymatic synthesis, CMP-7-F-sialic acid, Sugar nucleotide
ASJC Scopus subject areas
- Chemistry(all)
- Analytical Chemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Organic Chemistry
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In: Carbohydrate Research, Vol. 343, No. 12, 10.02.2008, p. 2075-2082.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Chemoenzymatic synthesis of CMP-N-acetyl-7-fluoro-7-deoxy-neuraminic acid
AU - Hartlieb, Sina
AU - Günzel, Almut
AU - Gerardy-Schahn, Rita
AU - Münster-Kühnel, Anja K.
AU - Kirschning, Andreas
AU - Dräger, Gerald
N1 - Funding information: We thank Dipl.-Biochem. Melanie Oschlies for her expertise and for supplying samples of the CMP-sialic acid synthetases from mouse and rainbow trout. This work was supported by the Deutsche Forschungsgemeinschaft (Grants Ki 397/8-1 and Ki 397/9-1; GE 801/6-1) and the Fonds der Chemischen Industrie.
PY - 2008/2/10
Y1 - 2008/2/10
N2 - 7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with d-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-d-mannosamine. Aldolase catalyzed transformation yielded the corresponding fluorinated sialic acid which was activated as CMP ester using three different synthetases in the presence as well as in the absence of pyrophosphatase which possesses inhibitory properties. Finally, conditions were optimized to perform a one-pot reaction starting from fluorinated mannosamine, which yielded the 7-fluoro-7-deoxy-CMP-sialic acid by incubation with three enzymes.
AB - 7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with d-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-d-mannosamine. Aldolase catalyzed transformation yielded the corresponding fluorinated sialic acid which was activated as CMP ester using three different synthetases in the presence as well as in the absence of pyrophosphatase which possesses inhibitory properties. Finally, conditions were optimized to perform a one-pot reaction starting from fluorinated mannosamine, which yielded the 7-fluoro-7-deoxy-CMP-sialic acid by incubation with three enzymes.
KW - Chemoenzymatic synthesis
KW - CMP-7-F-sialic acid
KW - Sugar nucleotide
UR - http://www.scopus.com/inward/record.url?scp=45049086802&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2008.02.003
DO - 10.1016/j.carres.2008.02.003
M3 - Article
C2 - 18353292
AN - SCOPUS:45049086802
VL - 343
SP - 2075
EP - 2082
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 12
ER -