M8527
4-Methylumbelliferyl α-L-fucopyranoside
fluorogenic, ≥97% (TLC), powder
别名:
4-Methylumbelliferyl alpha-L-fucopyranoside
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关于此项目
经验公式（希尔记法）:
C16H18O7
化学文摘社编号:
分子量:
322.31
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352204
EC Number:
259-098-0
MDL number:
Beilstein/REAXYS Number:
8160514
产品名称
4-Methylumbelliferyl α-L-fucopyranoside, ≥97% (TLC)
InChI key
CQKHENXHLAUMBH-CRLRYRHBSA-N
InChI
1S/C16H18O7/c1-7-5-12(17)23-11-6-9(3-4-10(7)11)22-16-15(20)14(19)13(18)8(2)21-16/h3-6,8,13-16,18-20H,1-2H3/t8-,13+,14+,15-,16-/m0/s1
SMILES string
C[C@@H]1O[C@@H](Oc2ccc3C(C)=CC(=O)Oc3c2)[C@@H](O)[C@H](O)[C@@H]1O
assay
≥97% (TLC)
form
powder
solubility
DMF: 100 mg/mL, clear, colorless to faintly yellow
fluorescence
λex 360 nm; λem 449 nm (Reaction product)
storage temp.
−20°C
Quality Level
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Application
4-Methylumbelliferyl α-L-fucopyranoside has been used:
- as a substrate in α-L-fucosidase 1 (α-L-FUCA-1) enzyme assays to convert it to the fluorescent product 4-methylumbelliferone (4MU) for finding the distribution of the membrane-associated α-L-FUCA-1 of human sperm
- as a fluorogenic substrate in enzyme assays to evaluate the stability of both the seminal plasma and membrane-associated α-l-fucosidase
- as a substrate to measure the enzymatic activity of α-L-FUCA-1 of cell extracts from TPC-1, BCPAP, 8505C, and CAL62 cell lines
General description
Substrate for α-L-fucosidase
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
法规信息
涉药品监管产品
此项目有
Giancarlo Vecchio et al.
Oncotarget, 8(16), 27075-27092 (2017-04-14)
Glycans containing α-L-fucose participate in diverse interactions between cells and extracellular matrix. High glycan expression on cell surface is often associated with neoplastic progression. The lysosomal exoenzyme, α-L-fucosidase-1 (FUCA-1) removes fucose residues from glycans. The FUCA-1 gene is down-regulated in
M Masserini et al.
The Biochemical journal, 229(3), 595-603 (1985-08-01)
alpha-L-Fucosidase, prepared in highly purified form (Mr 70 000-74 000) from Octopus hepatopancreas, was able to hydrolyse a fucose-containing ganglioside, namely Fuc-GM1 (II3NeuAc,IV2Fuc-GgOse4-Cer). The enzyme showed an irregular kinetic behaviour (v/[S] and v/[E] relationships following sigmoidal curves) when working on
Crypticity and functional distribution of the membrane associated alpha-L-fucosidase of human sperm.
Jennifer J Venditti et al.
Molecular reproduction and development, 74(6), 758-766 (2006-11-30)
Two distinctive isoforms of the enzyme alpha-L-fucosidase are found within human semen in substantial amounts, suggesting specialized functions during reproduction. The membrane-associated isozyme of human sperm cells was previously characterized biochemically, and here we report on its subcellular localization. Intact
A Giuliani et al.
Glycoconjugate journal, 10(6), 447-452 (1993-12-01)
The behaviour of a highly purified alpha-L-fucosidase (E.C. 3.2.1.51) extracted from octopus hepatopancreas was studied with phospholipid vesicles composed of phosphatidylcholine (PC) and phosphatidylserine (PS) containing the fucosylated ganglioside FucGM1, a potential natural substrate of the enzyme. The substrate recognition
Jennifer J Venditti et al.
International journal of andrology, 32(5), 556-562 (2008-06-05)
Previous reports from this laboratory documented the existence of two novel isoforms of alpha-L-fucosidase in human semen and showed that membrane-associated alpha-L-fucosidase is cryptically held within the acrosomal compartment and enriched within the sperm equatorial segment. The occurrence of these
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