DOI: 10.1111/j.1432-1033.1993.tb18197.x. The use of human milk fucosyltransferase in the synthesis of tumor‐associated trimeric X determinants

The use of human milk fucosyltransferase in the synthesis of tumor‐associated trimeric X determinants

10.1111/j.1432-1033.1993.tb18197.x

Crossref journal-article

Wiley

European Journal of Biochemistry (311)

Abstract

We have studied the fucosylaticn of a chemically synthesized trimer of N‐acetyllactosamine [(LacNAc)3‐EtPhNHCOCF3] with a fucosyltransferase preparation from normal human milk, which utilizes both type‐1 and type‐2 structures, whether sialylated or not. When fucose residues were added enzymically to the (LacNAc)3‐EtPhNHCOCF3 hexasaccharide, mono‐, di‐, or trifucosylated oligosaccharide species were formed, containing the Lewisx determinant (Galβ1→4[Fucα1→3]GlcNAcβ1→3). With excess GDP‐fucose and prolonged reaction times, the trifucosylated product was formed in almost quantitative yield. Kinetic analysis of the fucosylation reaction indicated that there is a significant difference in the rate of transfer of the first, second and third fucose residues onto the acceptor molecule. The location of the fucose residues in the monofucosylated and difucosylated intermediate products was assessed by analyzing the digests obtained after endo‐β‐galactosidase treatment by HPLC and reverse‐phase chromatography. In addition, the fucosylated (LacNAc)3‐EtPhNHCOCF3, structures were characterized by HPLC and were identified by 400‐MHz 1H‐NMR spectroscopy. There is a highly preferred order in which the fucosyl residues are attached to (LacNAc)3‐EtPhNHCOCF3. In the major pathway, the first two fucose residues are transferred with equal preference to the medial (GN3) and proximal (GN1) GlcNAc residues, whereas the third fucose is attached to the distal (GN5) GlcNAc residue. These results are of relevance in understanding the role of α‐3‐fucosyltransferase in the biosynthesis of Lewisx‐related cell‐surface carbohydrate structures, that function as ligands for selectin‐type cell‐adhesion molecules and may play a role in the invasion and metastasis of several carcinoma.

Bibliography

De VRIES, T., NORBERG, T., LÃNN, H., & VAN DEN EIJNDEN, D. H. (1993). The use of human milk fucosyltransferase in the synthesis of tumorâassociated trimeric X determinants. European Journal of Biochemistry, 216(3), 769â777. Portico.

Authors 4

Theodora De VRIES (first)
Thomas NORBERG (additional)
Hans LÖNN (additional)
Dirk H. VAN DEN EIJNDEN (additional)

References 47 Referenced 26

10.1016/S0021-9258(17)43099-7
10.1016/S0021-9258(17)39654-0
10.1038/292156a0
10.1038/314053a0
10.1016/S0021-9258(18)90602-2
10.1126/science.1701274
10.1126/science.1701275
10.1016/0092-8674(90)90444-J
10.1016/S0021-9258(17)38819-1 / J. Biol. Chem. by Fukuda M. (1985)
10.1016/0014-4827(91)90451-Y
10.1016/0006-291X(91)92068-U
{'key': 'e_1_2_3_13_2', 'first-page': '7619', 'volume': '261', 'author': 'Holmes E. H.', 'year': '1986', 'journal-title': 'J. Biol. Chem.'} / J. Biol. Chem. by Holmes E. H. (1986)
10.1016/0008-6215(88)80099-5
10.1111/j.1432-1033.1990.tb19107.x
10.1016/S0021-9258(18)90848-3
10.1093/glycob/1.6.577
10.1007/BF01046347
10.1016/S0006-291X(05)81472-X
10.1016/S0021-9258(18)45942-X
10.1042/bst0131119 / Biochem. Soc. Trans. by Johnson P. H. (1985)
10.1016/S0021-9258(19)50641-X
10.1016/S0021-9258(18)35803-4
10.1016/S0021-9258(19)68643-6
10.1101/gad.4.8.1288
10.1016/S0021-9258(19)67827-0
10.1016/S0021-9258(19)47396-1
10.1182/blood.V81.11.2978.2978
10.1016/0003-9861(89)90479-7
10.1016/S0021-9258(18)45459-2
10.1080/07328308908048021
10.1080/07328309008545794 / J. Carbohydr. Chem. by Nilsson M. (1990)
10.1139/v90-165
10.1016/0005-2795(73)90180-3
10.1016/0003-9861(69)90148-9
10.1515/bchm2.1981.362.1.113
10.1007/BF01047893
10.1016/S0021-9258(18)89163-3
10.1016/S0021-9258(18)33363-5
10.1351/pac198153010045
10.1016/S0338-4535(86)80018-6
{'key': 'e_1_2_3_42_2', 'first-page': '15', 'volume': '5', 'author': 'Caillard T.', 'year': '1988', 'journal-title': 'Exp. Clin. Immunogenet.'} / Exp. Clin. Immunogenet. by Caillard T. (1988)
10.1007/BF00731136
10.1007/BF00731137
10.1006/abbi.1993.1132
10.1016/S0021-9258(20)71209-3
10.1016/S0021-9258(19)81495-3 / J. Biol. Chem. by Macher B. A. (1988)
10.1016/S0065-230X(08)60215-8

Dates

Type	When
Created	20 years, 6 months ago (March 4, 2005, 1:48 a.m.)
Deposited	1 year, 11 months ago (Oct. 1, 2023, 8:37 p.m.)
Indexed	3 weeks, 6 days ago (Aug. 7, 2025, 4:54 a.m.)
Issued	32 years ago (Sept. 1, 1993)
Published	32 years ago (Sept. 1, 1993)
Published Online	20 years, 6 months ago (March 3, 2005)
Published Print	32 years ago (Sept. 1, 1993)

Funders 0

None

BibTeX

@article{De_VRIES_1993, title={The use of human milk fucosyltransferase in the synthesis of tumor‐associated trimeric X determinants}, volume={216}, ISSN={1432-1033}, url={http://dx.doi.org/10.1111/j.1432-1033.1993.tb18197.x}, DOI={10.1111/j.1432-1033.1993.tb18197.x}, number={3}, journal={European Journal of Biochemistry}, publisher={Wiley}, author={De VRIES, Theodora and NORBERG, Thomas and LÖNN, Hans and VAN DEN EIJNDEN, Dirk H.}, year={1993}, month=sep, pages={769–777} }

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