Efficient synthesis of two HNK-1 related pentasaccharides

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1315-1318

  Belot, Frederic ^a   Otter, Albin ^b   Fukuda, Minoru ^a   Hindsgaul, Ole ^a,b  

^a BURNHAM INSTITUTE   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

HNK 1; N glycans; Pentassacharides

Indexed keywords

DISACCHARIDE; GLYCAN DERIVATIVE; PENTASACCHARIDE; TRISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DEPROTECTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0038780127     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40324     Document Type: Article

References (12)

1. Voshol, H.; van Zuylen, C. W. E. M.; Orberger, G.; Vliegenthart, J. F. G.; Schachner, M. J. Biol. Chem. 1996, 271, 22957.
2. Coutant, C.; Jacquinet, J.-C. J. Chem. Soc., Perkin Trans. 1 1995, 1573.
3. Blatter, G.; Beau, J.-M.; Jacquinet, J.-C. Carbohydr. Res. 1994, 260, 189.
4. Debenham, S. D.; Toone, E. J. Tetrahedron: Asymmetry 2000, 11, 385.
5. Li, Z.-J.; Li, H.; Cai, M.-S. Carbohydr. Res. 1999, 320, 1.
6. McAuliffe, J. C.; Fukuda, M.; Hindsgaul, O. Bioorg. Med. Chem. Lett. 1999, 9, 2855.
7. Sriv́astava, G.; Hindsgaul, O. Carbohydr. Res. 1992, 224, 83.
8. Lucas, H.; Basten, J. E. M.; Van Dinther, T. G.; Meulemenn, D. G.; Van Aelst, S. F.; Van Boeckel, C. A. A. Tetrahedron 1990, 46, 8207.
9. 2O at 600 MHz, and 27.0±0.1 °C; concentration ca. 8 mM; chemical shifts are relative to external 0.1% acetone set at 2.225 ppm measured in a separate sample under identical experimental conditions. Even under strict temperature control, chemical shifts are not reproducible to three decimals, however, within a given experiment at 600 MHz, signals can be distinguished accurately to this precision.
10. Correct glycosidic linkages are confirmed by the following inter-residue NOEs (s for strong, m for medium and w for weak interactions). 1: H1βGlcA-H3βGal (s) and H1βGlcA-H4Gal (m); H1βGal-H4βGlcNAc (likely s, overlaps with H1/H5βGal); H1βGlcNAc-H6a/bαMan (s) and H1βGlcNAc-H5αMan (w); H1αMan-H6bβMan (s) and H1αMan-H6aβMan (w) and H1αMan-H5βMan (w). 2: H1βGlcA-H3βGal (s) and H1βGlcA-H4βGal (m); H1βGal-H4βGlcNAc (likely s, overlaps with H1/H5βGal); H1βGlcNAc-H2αMan (s) and H1βGlcNAc-H1αMan (s); H1αMan-H6bβMan (s) and H1αMan-H6aβMan (w) and H1αMan-H5βMan (w). Furthermore, typical H1-H3 and H1-H5 intra-residue NOEs were observed for all β-glycosides. Taken together with the coupling constants, this confirms that all pyranose rings adopt the normal chair form.
11. 27 (1 and 2): 1018.3955; found 1: 1018.3961; 2:1018.3959
12. Bock, K.; Duus, J. O. J. Carbohydr. Chem. 1994, 13, 513.