By Hong-Yang Chuang
This thesis specializes in the synthesis and vaccine overview of the prostate tumor- linked carbohydrate antigen RM2. the writer first offers using the [1+2+3] one-pot sequential technique to effectively synthesise the RM2 antigen and its analogues as unmarried stereoisomers in each glycosylation step, generating stable yields and stereoselectivity. He then introduces the conjugation of the unreal RM2 antigen to the service protein CRM197 in a typical variety of 1–10 to create the prostate melanoma vaccine candidate, that is mixed with α-galactosylceramide C1, its analogue C34, or Alu. the result of the vaccination reports in mice also are defined and point out that the most powerful anti-RM2 antigen titer is exhibited whilst one molecule of diphtheria toxin (DT) is conjugated with a typical of 4.7 molecules of RM2 antigen (DT-RM4.7) and adjuvanted with the glycolipid C34. extra importantly, the brought about mouse antibodies mediate the powerful complement-dependent cytotoxicity (CDC) opposed to the prostate melanoma cellphone line LNCap. The research offered during this thesis is the 1st ever to effectively synthesize this advanced glycan molecule. as a result of the steric obstacle of the adjoining sialyl moiety, the advent of 2 sialic acid devices to the compact and inflexible 3,4 di branched galactoside unit is especially not easy and the β-selective and effective glycosylation of the galactosamine moiety on the 4-position of di branched galactose can also be problematic.
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Extra info for Synthesis and Vaccine Evaluation of the Tumor Associated Carbohydrate Antigen RM2 from Prostate Cancer
The reaction mixture was stirred at room temperature for 8 h under argon. The solution was concentrated to syrup which was extracted with dichloromethane. The extract was successively washed with 2 N HCl, water, NaHCO3(aq) and water, dried with Na2SO4 and concentrated. 85 g, 91 % yield). 9. 0631. 96 mmole) in pyridine (15 mL) at 0 °C. The mixture was stirred for 12 h at 40 °C, and methanol (5 mL) was added. The solution was concentrated into syrup and 28 1 Chemical Synthesis of Proposed RM2 and Derivatives extracted with dichloromethane.
0 mL) was slowly added to the reaction mixture. 324 mmole). After 2 h, when TLC indicated that acceptor 1-5 was fully consumed, the reaction was neutralized by triethylamine, diluted with dichloromethane, and ﬁltered with a pad of Celite. The ﬁltrate was poured into a mixture of saturated aq. NaHCO3 and saturated aq. Na2S2O3. The aqueous layer was extracted with two portions of ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, ﬁltered, and concentrated in vacuo. 5 ethylacetate/hexane) to give trisaccharide as white solid.
DEPT 135 (distortionless enhancement by polarization transfer) was employed for determination of multiplicity. Data were represented as follows: chemical shift, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad), coupling constant (J) in Hz, and integration. High resolution mass spectra were obtained using BioTOF III, and MALDI-TOF MS were obtained using Ultraflex II TOF/TOF. 85 mmole) was cooled to −20 °C, dissolved in BH3THF complex (36 mL, 1 M solution in THF), and treated with Bu2BOTf (13 mL, 1 M solution in CH2Cl2).
Synthesis and Vaccine Evaluation of the Tumor Associated Carbohydrate Antigen RM2 from Prostate Cancer by Hong-Yang Chuang