Highly efficient chemoenzymatic synthesis of naturally occurring and non-natural alpha-2,6-linked sialosides: a P. damsela alpha-2,6-sialyltransferase with extremely flexible donor-substrate specificity.
作者信息
Yu Hai, Huang Shengshu, Chokhawala Harshal, Sun Mingchi, Zheng Haojie, Chen Xi
机构信息
Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, CA 95616, USA.
出版信息
Angew Chem Int Ed Engl. 2006 Jun 12;45(24):3938-44. doi: 10.1002/anie.200600572.
Abstract
摘要
相似文献
1
Highly efficient chemoenzymatic synthesis of naturally occurring and non-natural alpha-2,6-linked sialosides: a P. damsela alpha-2,6-sialyltransferase with extremely flexible donor-substrate specificity.
Angew Chem Int Ed Engl. 2006 Jun 12;45(24):3938-44. doi: 10.1002/anie.200600572.
2
Trans-sialidase activity of Photobacterium damsela alpha2,6-sialyltransferase and its application in the synthesis of sialosides.
Glycobiology. 2010 Feb;20(2):260-8. doi: 10.1093/glycob/cwp172. Epub 2009 Oct 30.
3
Crystal structures of sialyltransferase from Photobacterium damselae.
FEBS Lett. 2014 Dec 20;588(24):4720-9. doi: 10.1016/j.febslet.2014.11.003. Epub 2014 Nov 15.
4
Purification and characterization of a marine bacterial beta-galactoside alpha 2,6-sialyltransferase from Photobacterium damsela JT0160.
J Biochem. 1996 Jul;120(1):104-10. doi: 10.1093/oxfordjournals.jbchem.a021370.
5
A recombinant α-(2→3)-sialyltransferase with an extremely broad acceptor substrate specificity from Photobacterium sp. JT-ISH-224 can transfer N-acetylneuraminic acid to inositols.
Carbohydr Res. 2010 Nov 22;345(17):2485-90. doi: 10.1016/j.carres.2010.09.022. Epub 2010 Sep 25.
6
A beta-galactoside alpha2,6-sialyltransferase produced by a marine bacterium, Photobacterium leiognathi JT-SHIZ-145, is active at pH 8.
Glycobiology. 2007 Nov;17(11):1167-74. doi: 10.1093/glycob/cwm086. Epub 2007 Aug 17.
7
Purification, cloning, and expression of an alpha/beta-galactoside alpha-2,3-sialyltransferase from a luminous marine bacterium, Photobacterium phosphoreum.
J Biol Chem. 2007 Oct 12;282(41):29794-802. doi: 10.1074/jbc.M701907200. Epub 2007 Aug 16.
8
Crystal structure of Vibrionaceae Photobacterium sp. JT-ISH-224 alpha2,6-sialyltransferase in a ternary complex with donor product CMP and acceptor substrate lactose: catalytic mechanism and substrate recognition.
Glycobiology. 2008 Jan;18(1):66-73. doi: 10.1093/glycob/cwm119. Epub 2007 Oct 25.
9
Crystal structure of alpha/beta-galactoside alpha2,3-sialyltransferase from a luminous marine bacterium, Photobacterium phosphoreum.
FEBS Lett. 2009 Jun 18;583(12):2083-7. doi: 10.1016/j.febslet.2009.05.032. Epub 2009 May 23.
10
Photobacterium sp. JT-ISH-224 produces two sialyltransferases, alpha-/beta-galactoside alpha2,3-sialyltransferase and beta-galactoside alpha2,6-sialyltransferase.
J Biochem. 2008 Feb;143(2):187-97. doi: 10.1093/jb/mvm208. Epub 2007 Nov 4.
引用本文的文献
1
Chemoenzymatic synthesis of sialylated and fucosylated mucin analogs reveals glycan-dependent effects on protein conformation and degradation.
RSC Chem Biol. 2025 Jul 14. doi: 10.1039/d5cb00111k.
2
Chemical and Enzymatic Synthesis of DisialylGb5 and Other Sialosides for Glycan Array Assembly and Evaluation of Siglec-Mediated Immune Checkpoint Inhibition.
Molecules. 2025 May 22;30(11):2264. doi: 10.3390/molecules30112264.
3
A New Strategy to Functionalize Exosomes via Enzymatic Engineering of Surface Glycans and its Application to Profile Exosomal Glycans and Endocytosis.
Adv Sci (Weinh). 2025 May;12(18):e2415942. doi: 10.1002/advs.202415942. Epub 2025 Mar 19.
4
EASyMap-Guided Stepwise One-Pot Multienzyme (StOPMe) Synthesis and Multiplex Assays Identify Functional Tetraose-Core-Human Milk Oligosaccharides.
JACS Au. 2025 Jan 27;5(2):822-837. doi: 10.1021/jacsau.4c01094. eCollection 2025 Feb 24.
5
Sugar Auxiliary Group Assisted Diversity-Oriented Enzymatic Modular Synthesis of 0-Series Ganglioside Glycans.
Angew Chem Int Ed Engl. 2025 Feb 10;64(7):e202418929. doi: 10.1002/anie.202418929. Epub 2025 Jan 7.
6
Enzyme-Sialylation-Controlled Chemical Sulfation of Glycan Epitopes for Decoding the Binding of Siglec Ligands.
J Am Chem Soc. 2024 Oct 30;146(43):29469-29480. doi: 10.1021/jacs.4c08817. Epub 2024 Oct 17.
7
Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides.
Org Lett. 2024 Oct 4;26(39):8272-8277. doi: 10.1021/acs.orglett.4c02899. Epub 2024 Sep 23.
8
Enzymatic Synthesis of Disialyllacto-N-Tetraose (DSLNT) and Related Human Milk Oligosaccharides Reveals Broad Siglec Recognition of the Atypical Neu5Acα2-6GlcNAc Motif.
Angew Chem Int Ed Engl. 2024 Dec 16;63(51):e202411863. doi: 10.1002/anie.202411863. Epub 2024 Oct 24.
9
Chemoenzymatic Synthesis of Sulfated -Glycans Recognized by Siglecs and Other Glycan-Binding Proteins.
JACS Au. 2024 Jul 26;4(8):2966-2978. doi: 10.1021/jacsau.4c00307. eCollection 2024 Aug 26.
10
Broad-Spectrum Legionaminic Acid-Specific Antibodies in Pooled Human IgGs Revealed by Glycan Microarrays with Chemoenzymatically Synthesized Nonulosonosides.
Molecules. 2024 Aug 22;29(16):3980. doi: 10.3390/molecules29163980.
本文引用的文献
1
Identification of a sialate O-acetyltransferase from Campylobacter jejuni: demonstration of direct transfer to the C-9 position of terminalalpha-2, 8-linked sialic acid.
J Biol Chem. 2006 Apr 28;281(17):11480-6. doi: 10.1074/jbc.M512183200. Epub 2006 Feb 14.
2
A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries.
J Am Chem Soc. 2005 Dec 21;127(50):17618-9. doi: 10.1021/ja0561690.
3
Chemoenzymatic synthesis of CMP-sialic acid derivatives by a one-pot two-enzyme system: comparison of substrate flexibility of three microbial CMP-sialic acid synthetases.
Bioorg Med Chem. 2004 Dec 15;12(24):6427-35. doi: 10.1016/j.bmc.2004.09.030.
4
Discovery and characterization of sialic acid O-acetylation in group B Streptococcus.
Proc Natl Acad Sci U S A. 2004 Jul 27;101(30):11123-8. doi: 10.1073/pnas.0403010101. Epub 2004 Jul 19.
5
Chemically defined sialoside scaffolds for investigation of multivalent interactions with sialic acid binding proteins.
J Org Chem. 2003 Oct 31;68(22):8485-93. doi: 10.1021/jo030203g.
6
Evidence of regio-specific glycosylation in human intestinal mucins: presence of an acidic gradient along the intestinal tract.
J Biol Chem. 2003 Nov 21;278(47):46337-48. doi: 10.1074/jbc.M302529200. Epub 2003 Sep 2.
7
Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: a sialylated antigenic epitope of small-cell lung cancer.
Proc Natl Acad Sci U S A. 2003 Feb 4;100(3):797-802. doi: 10.1073/pnas.0337590100. Epub 2003 Jan 27.
8
Synthesis of sugar arrays in microtiter plate.
J Am Chem Soc. 2002 Dec 4;124(48):14397-402. doi: 10.1021/ja020887u.
9
Efficient chemoenzymatic synthesis of O-linked sialyl oligosaccharides.
J Am Chem Soc. 2002 May 22;124(20):5739-46. doi: 10.1021/ja017881+.
10
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
J Org Chem. 2002 May 3;67(9):3057-64. doi: 10.1021/jo011148j.
Zotero 插件