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Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)

NCBI PubMed ID: 16662430
Publication DOI: 10.1104/pp.70.1.12
Journal NLM ID: 0401224
Publisher: American Society of Plant Biologists
Institutions: Department of Biochemistry, The University of Texas Health Science Center, San Antonio, Texas 78284

Lipid-linked oligosaccharides were synthesized with the particulate enzyme preparation from mung bean (Phaseolus aureus) seedlings in the presence of GDP-[(14)C] mannose. The oligosaccharides were released from the lipids by mild acid hydrolysis and purified by several passages on Biogel P-4 columns. Five different oligosaccharides were purified in this way. Based on their relative elution constants (K(d)) compared to a variety of standard oligosaccharides, they were sized as (mannose-acetylglucosamine) Man(7)GlcNAc(2), Man(5)GlcNAc(2), Man(3)GlcNAc(2), Man(2)GlcNAc(2), and ManGlcNAc(2). These oligosaccharides were treated with endoglucosaminidase H and α- and β-mannosidase, and the products were examined on Biogel P-4 columns. They also were subjected to a number of chemical treatments including analysis of the reducing sugar by NaB(3)H(4) reduction, methylation analysis, and in some cases acetolysis. From these data, the likely structures of these oligosaccharides are as follows: E, Manβ-GlcNAc-GlcNAc; D, Manα1→3Manβ-GlcNAc-GlcNAc; C, Manα1→2Manα1→3Manβ-GlcNAc-GlcNAc; B, Manα1→2Manα1→2Manα1→3(Manα1→6)Manβ-GlcNAc-GlcNAc; and A, Manα1→2Manα1→2Manα1→3(Manα1→[Manα1→6]Manα1→6)Manβ-GlcNAc-GlcNAc. The synthesis of the Man(7)GlcNAc(2) was greatly diminished when tunicamycin (10 mug/ml) was added to the incubation mixtures.

Structure type: oligomer
Location inside paper: fig. 12, B
Compound class: N-glycan
Contained glycoepitopes: IEDB_123886,IEDB_130701,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_150077,IEDB_151531,IEDB_152206,IEDB_153212,IEDB_540671,IEDB_548907,IEDB_983930,SB_136,SB_196,SB_197,SB_198,SB_33,SB_44,SB_67,SB_72,SB_73,SB_74,SB_85

Methods: gel filtration, TLC, acid hydrolysis, enzymatic digestion, methylation analysis, PC, enzymatic assay
Comments, role: proposed structure

NCBI Taxonomy refs (TaxIDs): 3916
Reference(s) to other database(s): CCSD:13162, CBank-STR:16486
Show glycosyltransferases

There is only one chemically distinct structure:

[1*]OP(=O)(O)OP(=O)(O)OC1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H]3O)[C@H](O)[C@H]2NC(C)=O)[C@H](O)[C@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize

R1 = dolichol