| One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities. | |
| | |
MedLine Citation:
|
PMID: 17406495 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
Chemoenzymatic synthesis, which combines the flexibility of chemical synthesis and the high selectivity of enzymatic synthesis, is a powerful approach to obtain complex carbohydrates. It is a preferred method for synthesizing sialic acid-containing structures, including those with diverse naturally occurring and non-natural sialic acid forms, different sialyl linkages and different glycans that link to the sialic acid. Starting from N-acetylmannosamine, mannose or their chemically or enzymatically modified derivatives, sialic acid aldolase-catalyzed condensation reaction leads to the formation of sialic acids and their derivatives. These compounds are subsequently activated by a CMP-sialic acid synthetase and transferred to a wide range of suitable acceptors by a suitable sialyltransferase for the formation of sialosides containing natural and non-natural functionalities. The three-enzyme coupled synthesis of sialosides can be carried out in one pot without the isolation of intermediates. The time for synthesis is 4-18 h. Purification and characterization of the product can be completed within 2-3 d. |
| | |
Authors:
|
Hai Yu; Harshal A Chokhawala; Shengshu Huang; Xi Chen |
Related Documents
:
|
20354005 - Identification of glycoproteins targeted by trypanosoma cruzi trans-sialidase, a virule... 2005385 - The presence of sialidase-sensitive sialosylgangliotetraosyl ceramide (gm1b) in stimula... 7402355 - Removal of sialic acid from cardiac sarcolemma does not affect contractile function in ... 6097135 - Changes in (na+ + k+) atpase activity and the composition of surface carbohydrates in e... 18343205 - Direct involvement of the tumor suppressor p53 in nucleotide excision repair. 20354005 - Identification of glycoproteins targeted by trypanosoma cruzi trans-sialidase, a virule... |
Publication Detail:
|
Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: Nature protocols Volume: 1 ISSN: 1750-2799 ISO Abbreviation: Nat Protoc Publication Date: 2006 |
Date Detail:
|
Created Date: 2007-04-04 Completed Date: 2007-10-23 Revised Date: 2011-09-26 |
Medline Journal Info:
|
Nlm Unique ID: 101284307 Medline TA: Nat Protoc Country: England |
Other Details:
|
Languages: eng Pagination: 2485-92 Citation Subset: IM |
Affiliation:
|
Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, California 95616, USA. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Escherichia coli K12
/
enzymology Oxo-Acid-Lyases / metabolism Pasteurella multocida / enzymology Photobacterium / enzymology Sialic Acids / chemical synthesis*, chemistry*, isolation & purification Sialyltransferases / metabolism Trisaccharides / chemical synthesis*, chemistry, isolation & purification |
| Grant Support | |
ID/Acronym/Agency:
|
R01 GM076360-01/GM/NIGMS NIH HHS; R01GM076360/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
|
0/Sialic Acids; 0/Trisaccharides; EC 2.4.99.-/Sialyltransferases; EC 4.1.3.-/Oxo-Acid-Lyases; EC 4.1.3.3/N-acetylneuraminate lyase |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: IRAP and REMAP for retrotransposon-based genotyping and fingerprinting.
Next Document: Error-prone rolling circle amplification: the simplest random mutagenesis protocol.