Abstract
Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5037-5040 |
| Number of pages | 4 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 21 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 1 2011 |
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Keywords
- C8-modification
- Chemoenzymatic synthesis
- Sialic acid
- Sialoside
- Sialyltransferase
ASJC Scopus subject areas
- Pharmaceutical Science
- Drug Discovery
- Organic Chemistry
- Molecular Medicine
- Molecular Biology
- Clinical Biochemistry
- Biochemistry
Cite this
Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides. / Yu, Hai; Cao, Hongzhi; Tiwari, Vinod Kumar; Li, Yanhong; Chen, Xi.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 17, 01.09.2011, p. 5037-5040.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides
AU - Yu, Hai
AU - Cao, Hongzhi
AU - Tiwari, Vinod Kumar
AU - Li, Yanhong
AU - Chen, Xi
PY - 2011/9/1
Y1 - 2011/9/1
N2 - Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.
AB - Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.
KW - C8-modification
KW - Chemoenzymatic synthesis
KW - Sialic acid
KW - Sialoside
KW - Sialyltransferase
UR - http://www.scopus.com/inward/record.url?scp=80051795743&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=80051795743&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2011.04.083
DO - 10.1016/j.bmcl.2011.04.083
M3 - Article
VL - 21
SP - 5037
EP - 5040
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 17
ER -