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M8527

Sigma-Aldrich

4-Methylumbelliferyl α-L-fucopyranoside

≥97% (TLC)

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Synonym(s):
4-Methylumbelliferyl alpha-L-fucopyranoside
Empirical Formula (Hill Notation):
C16H18O7
CAS Number:
54322-38-2
Molecular Weight:
322.31
Beilstein:
8160514
EC Number:
259-098-0
MDL number:
MFCD00051218
PubChem Substance ID:
24897268

Quality Level

200

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

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

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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

Substrates

Substrate for α-L-fucosidase

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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
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
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
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
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
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