Answers to Chapter 7.pdf - Introduction to Bioorganic Chemistry and Chemical Biology Answers to Chapter 7(in-text asterisked problems Answer 7.1 O HO

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Unformatted text preview: Introduction to Bioorganic Chemistry and Chemical Biology Answers to Chapter 7 (in-text & asterisked problems) Answer 7.1 O HO sulfotransferase OR' HO O HO O S O OR -O O NHAc OR O O S -O O OR' and/or deacetylase NHAc O OR' HO O HO NH3+ HO NHAc OR' OR OR Introduction to Bioorganic Chemistry and Chemical Biology | A7145 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.2 design by © OH HO O HOO H OH O HO OH HO HO O H OH OH β-D-galactose β-D-xylose OH OH O O OH OH HO OR α-L-fucose α-D-mannose Introduction to Bioorganic Chemistry and Chemical Biology | A7146 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.3 design by © (S) O HO HO HO (R) O OH HO OH (R) OH CO2H HO H OH CO2H HO HO OH OH L-arabinose O OH D-sugar D-sugar Introduction to Bioorganic Chemistry and Chemical Biology | A7147 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.4 design by © Compounds with the strongest axial donor lone pair would exhibit the strongest preference for an axial OR group. A NH > O OR B N- > OR > OR OR N H > H N OR Has the strongest donor lone pair. Note: this species would be unstable toward SN1 > OR H +N H OR Introduction to Bioorganic Chemistry and Chemical Biology | A7148 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.5 design by © In lubiprostone, the CF2 group should favor the cyclic hemiketal relative to the parent compound with CH2. 1 2 Introduction to Bioorganic Chemistry and Chemical Biology: Answers to Chapter 7 Answer 7.6 The trend of faster hydrolysis of α-glucopyranosides holds for a wide range of glycosidic derivatives. Oddly, methyl α-d-glycosides (such as gluco, galacto, and xylo) hydrolyze more slowly than the corresponding β-anomers. O HO OPh HO OH OPh O HO HO OH OH OH β α HO HOO H O HO antibonding orbital .. O HO HOO H + OPh H HO +OPh H faster hydrolysis Introduction to Bioorganic Chemistry and Chemical Biology | A7190 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.7 design by © retaining HO HOO H O O H O .. OR HO -O HO HOO H O O O- O H + OR HO .. -O HO HOO H O O- O H :O HO O O HO HO O H H O O OH HO inverting HO HOO H O O H O .. OR HO HOO H HO O O- O H + OR HO O H -O O O HO HOO H H -O OH O O H O O R HO OH O Introduction to Bioorganic Chemistry and Chemical Biology | A7149 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.8 design by © OH HO B .. H B O OR' O HO O OH HO H O H AcHN O UDP•Mg H B R O .. HO O HO O H H AcHN O UDP•Mg ‡ H R O HO O HOO H sp2 H AcHN O UDP•Mg HO O O O H AcHN H OH HO O O OH OR' Introduction to Bioorganic Chemistry and Chemical Biology: Answers to Chapter 7 Answer 7.9 A B HO HO HO HO O 2 HO O βO O α HO O 3 β O NHAc 6 HO HO O 3 HO HO HO β O OH R HO HO HO 6 4 3 OH O 5 1 2 6 β O HO O 5 4 OH 3 1 2 β O 5 4 3 1 2 α O O O NH NHAc OH OH Galβ1–4GlcNAcβ1–2Manα–Ser Fucα1–2Galβ1–3GlcNAcβ1–3Galβ–OR Introduction to Bioorganic Chemistry and Chemical Biology | A7151 Answer Van Vranken7.10 & Weiss | 978-0-8153-4214-4 © design by OH OO O O NH H O HOO H OH HO O OH HO O O OH O OH O O O O O OH H O NH OH O Introduction to Bioorganic Chemistry and Chemical Biology | A7152 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.11 design by © This is simply an electrophilic aromatic substitution reaction. HO O HO HO OP OR R O O HO H O R + HO N H OH -A: N OH H HO Introduction to Bioorganic Chemistry and Chemical Biology | A7153 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.12 design by © The fucosyl, galactosyl, and sialyl subunits will generate at least one free aldehyde that is still attached to the IgG. HO α-D-sialyl HO H O R CO2H R'O O O O OR NaIO4 O RO O OH HO OR OH O NaIO4 O OH Introduction to Bioorganic Chemistry and Chemical Biology | A7176 Van Vranken & Weiss | 978-0-8153-4214-4 © design by OR OH O OH O H OR OH O O O HN detached OH HO β-L-fucosyl O HO NaIO4 HO HN O 6-glycosyl-β-D-galactosyl O OH R CO2H 3 4 Introduction to Bioorganic Chemistry and Chemical Biology: Answers to Chapter 7 Answer 7.13 HO O HO : NH2 Lys O HO O : NH OH OH O + H OH OH O O OH OH OH OH OH O : NH Lys NHAc OH OH OH OH CO2 + NH Lys NHAc O or : NH Lys NHAc OH OH NH Lys B: HO O + NH Lys H Lys HO O OH2+ Molecular modeling suggests that the carboxylic acid of pyruvic acid protonates the aldehyde carbonyl. OH O : OH2 CO2H OH OH NHAc Introduction to Bioorganic Chemistry and Chemical Biology | A7154 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.14 design by © -O O HOO H -O O O HOO H O OH -O O O OH O GlcAβ−ibuprofen O HOO H O GlcAβ(1-3)−morphine O O OH OMe N O GlcAβ−naproxen H HO Introduction to Bioorganic Chemistry and Chemical Biology | A7155 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.15 design by © Ar OR O O Ph O OO t-BuPh2Si Me S: Ar + O O O O t-BuPh2Si O Ph Ar O O Ph O OO t-BuPh2Si O Ph O t-BuPh2Si O S Me + Me H3C OTf H2O H O O O O t-BuPh2Si O Ph OR OR .. Ar .. O O O R + OR Introduction to Bioorganic Chemistry and Chemical Biology | A7156 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.16 design by © Ph O OO Bn Bn O O O H :B O OO Bn O OO O Bn O O F C S O S CF 3 3 O O: O Ph O OO Bn Bn O O O+ O OO Bn Bn O O O O Ph O Ph : O Ph O OO Bn Bn O O : OTf Introduction to Bioorganic Chemistry and Chemical Biology | A7157 Van Vranken & Weiss | 978-0-8153-4214-4 © design by Tf O Ph + O O OO Bn Bn HOR .. O O OTf Ph O OO Bn Bn O O OR Introduction to Bioorganic Chemistry and Chemical Biology: Answers to Chapter 7 Answer 7.17 OBn BnO OBn BnO O FmocO O PivO OBn BnO -OTf O OBu OBu O+ FmocO P OBu Me P OBu O O Me Si OTf .. .. O SiMe 3 t-Bu O Me not SN O FmocO O t-Bu 2 O FmocO OBn BnO OBn OBn BnO O O + t-Bu .. HO O Bn O OBn O FmocO OR O O Bn PivO PivO O+ O OR PivO Introduction to Bioorganic Chemistry and Chemical Biology | A7158 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.18 design by © NH .. 2 N O .. OH+ H NNH + 2 3 O OR N NH + HOR O OR Introduction to Bioorganic Chemistry and Chemical Biology | A7159 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.19 design by © H Fucα1 2Galβ1 4GlcNAcβ1 3Galβ1 4GlcNAcβ Galβ1 3 B Fucα1 2 Galβ1 4GlcNAcβ1 3Galβ1 4GlcNAcβ GalNAcβ1 3 A Galβ1 4GlcNAcβ1 3Galβ1 4GlcNAcβ Fucα1 2 Introduction to Bioorganic Chemistry and Chemical Biology | A7160 Van Vranken & Weiss | 978-0-8153-4214-4 design by © Answer 7.20 HO .. H A O OH HO H O + HO OH HO OH OH HO HO HO OH HO + NHR OH OH HO OH OH H O: HO H + H NHR O OH HO OH OH H : NHR O OH2 + HO OH .. H2NR .. + H O OH OH : A- H O + HO NHR HO OH O HO HO OH NHR OH OH OH Introduction to Bioorganic Chemistry and Chemical Biology | A7161 Van Vranken & Weiss | 978-0-8153-4214-4 Answer 7.21 design by © + NHR H O OH HO HO H : A- HO H O HO NHR H A OH : HO HO H O HO HO Introduction to Bioorganic Chemistry and Chemical Biology | A7162 Van Vranken & Weiss | 978-0-8153-4214-4 © design by OH H N R O H + HO : A- H O HO H N O OH R 5 6 Introduction to Bioorganic Chemistry and Chemical Biology: Answers to Chapter 7 Answer 7.22 B: H O O HO HO O HO OH HO - OH HO OH OH O: HO O H OH OH HO HO OH OH O H O .. - O H HO OH OH HO O .. OH OH .. HO H B :B HO OH O HO O HO OH OH OH OH Introduction to Bioorganic Chemistry and Chemical Biology | A7163 Van Vranken & Weiss | 978-0-8153-4214-4 7.23 design by ©*Answer B: H O O HO HO O HO OH HO O .. - HO OH OH OH OH O HO B O H OH OH HO .. HO OH HO O H HO OH OH O .. - HO O .. - :B O HO .. O- HO OH O OH HO O H B+ Introduction to Bioorganic Chemistry and Chemical Biology | A7164 Van Vranken & Weiss | 978-0-8153-4214-4 *Answer 7.24 © design by OH EtO 2C S S CO 2Et OH chair with axial OH groups Introduction to Bioorganic Chemistry and Chemical Biology | A7165 Van Vranken & Weiss | 978-0-8153-4214-4 *Answer 7.26 design by © HO OH O HO HO O HO OH OH O O OH OH HO O O O NHAc (CH2) 14CH3 OH O O O OH H HN O O (CH2) 12CH3 OH OH Introduction to Bioorganic Chemistry and Chemical Biology | A7167 Van Vranken &7.29 Weiss | 978-0-8153-4214-4 *Answer © design by O R O O OH OH O H NH O :B R O O O .. NH OH OH Introduction to Bioorganic Chemistry and Chemical Biology | A7170 Van Vranken & Weiss | 978-0-8153-4214-4 *Answer 7.32 design by © HO O O pyruvic acid Introduction to Bioorganic Chemistry and Chemical Biology | A7173 Van Vranken & Weiss | 978-0-8153-4214-4 © design by O R O .. O - OH OH OH + NH H B H H H - O R O O OH OH H 2O OH OH R O OH OH ...
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