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M8527

Sigma-Aldrich

4-Methylumbelliferyl α-L-fucopyranoside

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:
Molecular Weight:
322.31
Beilstein:
8160514
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.21

product name

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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