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Angewandte Chemie - International Edition

Volumn 46, Issue 27, 2007, Pages 5226-5230

Synthetic vaccines of tumor-associated glycopeptide antigens by immune-compatible thioether linkage to bovine serum albumin

(3) Wittrock, Sven a Becker, Torsten a Kunz, Horst a

a JOHANNES GUTENBERG UNIVERSITY (Germany)

Author keywords

Antigens; Glycopeptides; Proteins; Synthetic vaccines; Thiol additions

Indexed keywords

BOVINE SERUM ALBUMIN; GLYCOPEPTIDES; SYNTHETIC VACCINES; THIOETHER; THIOL ADDITIONS;

ADDITION REACTIONS; ANTIGENS; GLYCOPROTEINS; IMMUNIZATION; PHOTOCHEMICAL REACTIONS; TUMORS;

VACCINES;

BOVINE SERUM ALBUMIN; CANCER VACCINE; GLYCOPEPTIDE; RECOMBINANT VACCINE; SULFIDE; TUMOR ANTIGEN;

ANIMAL; ARTICLE; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; IMMUNOLOGY;

ANIMALS; ANTIGENS, NEOPLASM; CANCER VACCINES; CATTLE; GLYCOPEPTIDES; MOLECULAR STRUCTURE; SERUM ALBUMIN, BOVINE; SULFIDES; VACCINES, SYNTHETIC;

EID: 34447328219 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200700964 Document Type: Article

Times cited : (107)

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59
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- α]D23, 84.6 deg cm3 g -1 dm-1 (c, 0.02 g cm-3, H 2O, HR-ESI-MS (positive, m/z 1759.7931 [M+H, calcd 1759.7948. 1H NMR (400 MHz, D2O, COSY, δ, 5.29 (d, 1 H, J4,3, 2.9 Hz, H-4, 5.09 (dd, 1 H, J3,2, 11.2 Hz, H-3, 4.99 (d, 1 H, J 1,2, 3.7 Hz, H-1, 2.98 (t, 2 H, J, 6.8 Hz, S-CH 2, 2.84 (dd, 1 H, Jgem, 17.1 Hz, J vic, 6.5 Hz, Daβ, 2.79 (dd, 1H, Jvic, 6.8 Hz, Dbβ, 1.18 (d, 3 H, J, 6.3 Hz, Tγ, 1.06 ppm d, 3 H, J, 6.4 Hz, Tγ
- γ).

60
- 34447345040
- Experimental: In a quartz test tube (NS 14.5) 7a (11 mg, 6.9 μmol) was dissolved in degassed aqueous phosphate buffer (pH 7). Under argon atmosphere, 4 mg of olefin-modified BSA 5b was added. The solution was irradiated with a mercury low-pressure vapor lamp (λ = 254 nm, 77 W) for 6 h, dialysed against distilled water (Spectra/Por Float A Lyzer), and lyophilised to give 7 mg of 8a as a colorless lyophilisate. MALDI-MS (positive): m/z 83 23.6.
- Experimental: In a quartz test tube (NS 14.5) 7a (11 mg, 6.9 μmol) was dissolved in degassed aqueous phosphate buffer (pH 7). Under argon atmosphere, 4 mg of olefin-modified BSA 5b was added. The solution was irradiated with a mercury low-pressure vapor lamp (λ = 254 nm, 77 W) for 6 h, dialysed against distilled water (Spectra/Por Float A Lyzer), and lyophilised to give 7 mg of 8a as a colorless lyophilisate. MALDI-MS (positive): m/z 83 23.6.

61
- 34447342437
- α]D23, 63.8 deg cm3 g -1 dm-1 (c, 0.01 g cm-3, H 2O, HR-ESI-MS (positive, m/z 2604.0803 [M+H, calcd 2604.0931; 1H NMR (400 MHz, D2O, DQF-COSY, δ, 5.33-5.16 (m, 4 H [5.3, H-8″, 5.27} H-4, 5.26} H-7″, 5.23} CH2a-Bn-Ester, 5.00-4.86 (m, 3 H, 4.95} CH 2b-Bn-ester, 4.91} H-4′, 4.88} H-1, 2.93 (m, 2 H, S-CH 2, 2.85 (dd, 1 H, Jgem, 17.3 Hz, J vic, 6.6 Hz, Daβ, 1.21-1.13 (m, 3 H, Tγ*, 1.06 ppm (d, 3 H, J, 6.4 Hz, T γ, 13C NMR (100.6 MHz, D2O, HSQC, δ, 100.8 (C-1′, 98.9 (2C, C-1, C-2″, 36.8 (C-3″, 30.0 (SAc, 28.2 ppm S-CH2
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63
- 34447322187
- α]D25, 49.4 deg cm3 g -1 dm-1 (c, 0.01 g cm-3, H 2O, HR-ESI-MS: m/z 2118.9705 [M+H, calcd 2118.9760; 1H NMR (400 MHz, D2O, COSY, δ, 5.69 (m, 1 H, CH2-CH=CH2, 4.99 (m, 2 H, CH 2-CH=CH2, 4.80 (d, 1 H, J1,2, 3.7 Hz, H-1, 2.54 (dd, 1 H, J3,4, 4.5 Hz, J gem, 12.5 Hz, H-3′eq, 1.15 (d, 3 H, J, 6.2 Hz, Tγ*, 1.09-1.04 ppm (m, 6 H, 2 x Tγ, 13C NMR (100.6 MHz, D2O, HSQC, HMBC, δ, 133.6 (CH2-CH=CH2, 115.3 (CH2-CH=CH2, 99.3 (C-1, 99.2 (C-2′, 39.5 ppm C-3′
- 2), 99.3 (C-1), 99.2 (C-2′), 39.5 ppm (C-3′).

64
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