41239
D-Apiose solution
≥99.0% (HPLC)
Synonym(s):
3-C-Hydroxymethyl-D-glycero-tetrose
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About This Item
Empirical Formula (Hill Notation):
C5H10O5
CAS Number:
Molecular Weight:
150.13
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
Quality Level
assay
≥99.0% (HPLC)
concentration
100-1000 mM in H2O
storage temp.
room temp
SMILES string
OC[C@@]1(O)COC(O)[C@@H]1O
InChI
1S/C5H10O5/c6-1-5(9)2-10-4(8)3(5)7/h3-4,6-9H,1-2H2/t3-,4?,5+/m0/s1
InChI key
ASNHGEVAWNWCRQ-LJJLCWGRSA-N
Application
D-Apiose, a plant-specific branched-chain monosaccharide found in rhamnogalacturonan II (RG-II), apiogalacturonan, and several apioglycosides, serves as a borate binding site for crosslinking of galacturonans within plant cell walls.
Packaging
Pack size based on mg solid
Storage Class
12 - Non Combustible Liquids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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Joon-Woo Ahn et al.
The Journal of biological chemistry, 281(19), 13708-13716 (2006-03-22)
D-apiose serves as the binding site for borate cross-linking of rhamnogalacturonan II (RG-II) in the plant cell wall, and biosynthesis of D-apiose involves UDP-D-apiose/UDP-D-xylose synthase catalyzing the conversion of UDP-D-glucuronate to a mixture of UDP-D-apiose and UDP-D-xylose. In this study
A convenient synthesis of apiose.
M Koós et al.
Carbohydrate research, 146(2), 335-341 (1986-02-01)
C Hervé du Penhoat et al.
Journal of biomolecular NMR, 14(3), 253-271 (1999-09-11)
Rhamnogalacturonan II (RG-II) is a structurally complex pectic mega-oligosaccharide that is released enzymatically from the primary cell wall of higher plants. It contains roughly 30 monosaccharide units (MW approximately 5 kDa) including very unusual residues such as Kdo, Dha, aceric
Georg J Seifert
Current opinion in plant biology, 7(3), 277-284 (2004-05-12)
Plants possess a sophisticated sugar biosynthetic machinery comprising families of nucleotide sugar interconversion enzymes. Literature published in the past two years has made a major contribution to our knowledge of the enzymes and genes involved in the interconversion of nucleotide
Synthesis of an apiose-containing disaccharide fragment of rhamnogalacturonan-II and some analogues.
Anne-Laure Chauvin et al.
Carbohydrate research, 339(1), 21-27 (2003-12-09)
Beta-rhamnosylation of methyl 2-C-hydroxymethyl-2,3-O-isopropylidene-beta-D-erythrofuranoside and methyl 2,3-O-isopropylidene-beta-D-ribofuranoside was achieved using 4-O-acetyl-2,3-O-carbonyl-alpha-L-rhamnopyranosyl bromide and Ag2O as a promoter. Deprotected disaccharides beta-L-Rhap-(1-->3')-beta-D-Apif-OMe and beta-L-Rhap-(1-->3')-beta-D-Ribf-OMe were compared to their alpha-rhamnosyl isomers which were prepared using conventional Helferich glycosylation.
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