Abstract
Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-d-mannosamine (ManNAc) and the corresponding sialic acids from d-glucal were established. Lipase-catalyzed regioselective transformation of d-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tert-butyl alcohol proceeded in manno-configured at C-2 as well as α- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions.
| Original language | English |
|---|---|
| Pages (from-to) | 4284-4291 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 66 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - 2010 Jun 12 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group. / Calveras, Jordi; Nagai, Yasuhito; Sultana, Israt; Ueda, Yuji; Higashi, Toshinori; Shoji, Mitsuru; Sugai, Takeshi.
In: Tetrahedron, Vol. 66, No. 24, 12.06.2010, p. 4284-4291.Research output: Contribution to journal › Article
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TY - JOUR
T1 - New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group
AU - Calveras, Jordi
AU - Nagai, Yasuhito
AU - Sultana, Israt
AU - Ueda, Yuji
AU - Higashi, Toshinori
AU - Shoji, Mitsuru
AU - Sugai, Takeshi
PY - 2010/6/12
Y1 - 2010/6/12
N2 - Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-d-mannosamine (ManNAc) and the corresponding sialic acids from d-glucal were established. Lipase-catalyzed regioselective transformation of d-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tert-butyl alcohol proceeded in manno-configured at C-2 as well as α- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions.
AB - Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-d-mannosamine (ManNAc) and the corresponding sialic acids from d-glucal were established. Lipase-catalyzed regioselective transformation of d-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tert-butyl alcohol proceeded in manno-configured at C-2 as well as α- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions.
UR - http://www.scopus.com/inward/record.url?scp=77953590937&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77953590937&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.04.045
DO - 10.1016/j.tet.2010.04.045
M3 - Article
AN - SCOPUS:77953590937
VL - 66
SP - 4284
EP - 4291
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 24
ER -