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M8527

4-Methylumbelliferyl α-L-fucopyranoside

Name: 4-Methylumbelliferyl &#945;-<SC>L</SC>-fucopyranoside
Brand: SIGMA

fluorogenic, ≥97% (TLC), powder

Synonym(s):

4-Methylumbelliferyl alpha-L-fucopyranoside

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₈O₇

CAS Number:

54322-38-2

Molecular Weight:

322.31

NACRES:

NA.21

PubChem Substance ID:

24897268

UNSPSC Code:

12352204

EC Number:

259-098-0

MDL number:

MFCD00051218

Beilstein/REAXYS Number:

8160514

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Product Name

4-Methylumbelliferyl α-L-fucopyranoside, ≥97% (TLC)

Quality Level

200

assay

≥97% (TLC)

form

powder

solubility

DMF: 100 mg/mL, clear, colorless to faintly yellow

fluorescence

λ_ex 360 nm; λ_em 449 nm (Reaction product)

storage temp.

−20°C

SMILES string

C[C@@H]1O[C@@H](Oc2ccc3C(C)=CC(=O)Oc3c2)[C@@H](O)[C@H](O)[C@@H]1O

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

InChI key

CQKHENXHLAUMBH-CRLRYRHBSA-N

General description

Substrate for α-L-fucosidase

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品

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Stabilization of membrane-associated alpha-L-fucosidase by the human sperm equatorial segment.

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

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

Action of alpha-L-fucoside from Octopus vulgaris hepatopancreas on phospholipid vesicles containing the fucosylated ganglioside FucGM1.

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

Alpha-fucosidase-ganglioside interactions. Action of alpha-L-fucosidase from the hepatopancreas of Octopus vulgaris on a fucose-containing ganglioside (Fuc-GM1).

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

Human a-L-fucosidase-1 attenuates the invasive properties of thyroid cancer.

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

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Global Trade Item Number

SKU	GTIN
M8527-100MG	04061832909301
M8527-1MG	04061826676196
M8527-10MG	04061834063247
M8527-5MG	04061834063254
M8527-25MG	04061832909325

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