DOI: 10.1002/anie.199603211. Multiple Sialyl Lewis<sup>x</sup> N‐Glycopeptides: Effective Ligands for E‐Selectin

Multiple Sialyl Lewisx N‐Glycopeptides: Effective Ligands for E‐Selectin

10.1002/anie.199603211

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Bibliography

Sprengard, U., Schudok, M., Schmidt, W., Kretzschmar, G., & Kunz, H. (1996). Multiple Sialyl Lewisx NâGlycopeptides: Effective Ligands for EâSelectin. Angewandte Chemie International Edition in English, 35(3), 321â324. Portico.

Authors 5

Ulrich Sprengard (first)
Manfred Schudok (additional)
Wolfgang Schmidt (additional)
Gerhard Kretzschmar (additional)
Horst Kunz (additional)

References 45 Referenced 98

10.1016/0092-8674(94)90337-9
10.1002/jlb.55.5.662 / J. Leukocyte Biol. by Granger D. N. (1995)
10.1021/bi00253a021
10.1006/bbrc.1995.1568
10.1016/0968-0004(94)90109-0
10.1021/ja00106a008
10.1016/0040-4020(95)00833-T
10.1016/S0065-2318(08)60153-5
10.1002/ange.19881001212
10.1002/anie.198816971
10.1002/ange.19881000528
10.1002/anie.198807111
10.1002/ange.19951070121
10.1016/S0040-4039(00)80405-0
Solid‐phase synthesis on Sasrin resin: (a) 20% piperidine in DMF;
(b) 2 equiv temporarily blocked amino acid TBTU/HOBT/DIPEA (2 equiv each);
(c) TFA (1% in CH2Cl2) then pyridine 2a: 62%.
10.1021/ja00063a082
10.1021/ja01008a045
10.1111/j.1399-3011.1978.tb02869.x
10.1111/j.1399-3011.1978.tb02868.x
10.1021/ja00275a008
Characterization of7a: [α]= −41.3 (c= 1 in water);1H NMR (400 MHz D2O): δ = 1.33 (d 3H Jβ α= 7.3 Hz β‐Ala1) 1.36 (d 3H Jβ α= 7.3 Hz β‐Ala2) 2.66 (dd 1 H Jβ α= 7 Jgem= 16 Hz β‐Asp1) 2.71 (dd 1 H Jβ α= 7 Jgem= 16 Hz β‐Asp2) 2.73 (dd 1 H Jβ α= 7 Jgem= 16 Hz β‐Asp3) 2.76 (dd 1 H Jβ α= 7 Hz β‐Asp1) 2.85 (dd 1 H Jβ α= 7.2 Hz β‐Asp2) 2.94 (dd 1 H Jβ α= 6 Hz β‐Asp3) 3.84 (β‐Ser) 4.26 (m 2H α‐Ala1 α‐Ala2) 4.28 (dd 1 H α‐Ser) 4.52 (1 H α‐Asp3) 4.72 (1 H α‐Asp2) 4.79 (1 H α‐Asp1);13C NMR (125.8 MHz D2O): δ = 15.57 (β‐Ala2) 16.11 (β‐Ala1) 35.53 (β‐Asp1) 35.67 (β‐Asp1) 35.99 (β‐Asp3) 41.62 (α‐Gly) 49.27 (α‐Ala2) 49.78 (α‐Ala1) 49.08 49.19 50.57 (α‐Asp1 α‐Asp2 α‐Asp3) 55.24 (α‐Ser) 59.89 (β‐Ser) 170.46 170.57 (C  O1Ser) (C  O1Gly) 171.62 171.69 171.79 171.88 172.22 172.34 (C  O1Asp1) (C  O1Asp2) (C  O1Asp3) (C  O4Asp1) (C  O4Asp2) (C  O4Asp3) 174.3 (C  O Ala1) 174.70 (C  O Ala2); ESI‐MS: 1540 (M++ 2 Na)2+ 1034 (M++ 3 Na)3+.
{'key': 'e_1_2_1_16_2', 'first-page': '394', 'volume': '30', 'author': 'Barlos K.', 'year': '1989', 'journal-title': 'Tetrahedron Lett.'} / Tetrahedron Lett. by Barlos K. (1989)
Solid‐phase synthesis on TCP resin: (a) 20% piperidine in DMF;
(b) 3 equiv temporarily blocked amino acid HBTU/HOBT/DIPEA (3 equiv each);
(c) CH3COOH/CH3OH/CH2Cl2 2b: 36%.
10.1002/ange.19951070121
10.1002/anie.199500601
{'key': 'e_1_2_1_19_2', 'first-page': '221', 'volume': '107', 'author': 'Gall‐Istok K.', 'year': '1981', 'journal-title': 'Acta. Chim. Acad. Sci. Hung.'} / Acta. Chim. Acad. Sci. Hung. by Gall‐Istok K. (1981)
10.1016/0008-6215(84)85199-X
10.1016/0008-6215(90)80006-O
10.1248/cpb.39.2699
G. Arsequell.S. Y. C.Wong G. R.Guile T. W.Rademacher R. A.Dwek Abstr. Pap. Eur. Pept. Symp. 22nd(Interlaken Switzerland)1992. A416.
10.1016/0092-8674(91)90570-O
10.1016/S0021-9258(18)42453-2
W.Stahl U.Sprengard M.Ahlers B.Hörsch A.Walch G.Kretzschmar Tetrahedron Lett. submitted;B.Hörschet al. unpublished results.
Biophysical investigation of the neutrophile‐selectin interaction in hydrodynamic flow systems might improve out understanding of transient binding of clustered carbohydrate ligands and their receptors.
10.1517/13543784.3.7.709
10.1002/ange.19941062025
10.1002/anie.199420961
{'key': 'e_1_2_1_25_2', 'first-page': '441', 'volume': '337', 'author': 'Stahl W.', 'year': '1995', 'journal-title': 'Chem.'} / Chem. by Stahl W. (1995)
10.1021/jo00115a027
10.1002/ange.19951070920
10.1002/anie.199509901

Dates

Type	When
Created	21 years, 7 months ago (Jan. 16, 2004, 9:30 a.m.)
Deposited	1 year, 10 months ago (Oct. 26, 2023, 6:27 p.m.)
Indexed	1 year ago (Aug. 21, 2024, 8:45 p.m.)
Issued	29 years, 6 months ago (Feb. 16, 1996)
Published	29 years, 6 months ago (Feb. 16, 1996)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	29 years, 6 months ago (Feb. 16, 1996)

Funders 0

None

BibTeX

@article{Sprengard_1996, title={Multiple Sialyl Lewisx N‐Glycopeptides: Effective Ligands for E‐Selectin}, volume={35}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199603211}, DOI={10.1002/anie.199603211}, number={3}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Sprengard, Ulrich and Schudok, Manfred and Schmidt, Wolfgang and Kretzschmar, Gerhard and Kunz, Horst}, year={1996}, month=feb, pages={321–324} }

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