Introduction to Bioorganic Chemistry and Chemical Biology: Chapter 7 answers

Introduction to Bioorganic Chemistry and Chemical Biology 1




Answers to Chapter 7
(in-text & asterisked problems)



Answer 7.1
O OR'
sulfotransferase HO deacetylase
HO NHAc
O O OR
O OR' S O OR' O OR'
HO -O O HO




m
and/or




er as
O NHAc HO NHAc HO NH3+
S O OR OR OR




co
-O
O




eH w
Introduction to Bioorganic Chemistry and Chemical Biology | A7145
Van Vranken & Weiss | 978-0-8153-4214-4




o.
Answer 7.2
© www.garlandscience.com design by www.blink.biz

HO
OH

rs e OH
ou urc
HO OH
HOO O O HO O O
OH HO OH O OH
H OH OH H OH
OR HO
β-D-xylose β-D-galactose α-D-mannose α-L-fucose
o

Introduction to Bioorganic Chemistry and Chemical Biology | A7146
Van Vranken & Weiss | 978-0-8153-4214-4
aC s

Answer 7.3
© www.garlandscience.com design by www.blink.biz
vi y re


(S) HO (R) HO
O OH (R) H OH
OH O CO2H O CO2H
HO
HO
HO OH HO OH HO
ed d




OH OH
L-arabinose D-sugar D-sugar
ar stu




Introduction to Bioorganic Chemistry and Chemical Biology | A7147
Van Vranken & Weiss | 978-0-8153-4214-4
Answer 7.4
© www.garlandscience.com design by www.blink.biz

Compounds with the strongest axial donor lone pair would exhibit the strongest
is




preference for an axial OR group.
Th




A NH O
> >
OR OR OR
sh




H H
B N- N H
N +N
> > > H
OR OR
OR OR
Has the strongest donor lone
pair. Note: this species would
be unstable toward SN1
Introduction to Bioorganic Chemistry and Chemical Biology | A7148
Van Vranken & Weiss | 978-0-8153-4214-4
Answer 7.5
© www.garlandscience.com design by www.blink.biz

In lubiprostone, the CF2 group should favor the cyclic hemiketal relative to the parent
compound with CH2.
This study source was downloaded by 100000763811389 from CourseHero.com on 04-29-2021 03:50:20 GMT -05:00


https://www.coursehero.com/file/37863454/Answers-to-Chapter-7pdf/

, 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 OPh O OPh
HO HO

HO OH HO OH
OH OH
β α
.. antibonding
HO HO O orbital
HOO O + HOO
OPh
H HO H HO
H
+OPh
H
faster hydrolysis
Introduction to Bioorganic Chemistry and Chemical Biology | A7190
Van Vranken & Weiss | 978-0-8153-4214-4
Answer 7.7
© www.garlandscience.com design by www.blink.biz




m
retaining




er as
O O O O- O O-




co
H




eH w
H
HO HO H HO :O
HOO O .. HOO O + HOO O HO
H




o.
OR OR HO O
H HO H HO .. H HO O OH


rs e -O O -O O
O O H HO
ou urc
o
inverting
aC s

O O O O- O O-
vi y re


H
H
HO HO H HO
HOO O .. HOO O + HOO O O
OR OR R
H HO H HO H HO
H OH
O
ed d




H H
ar stu




-O O -O O O O


Introduction to Bioorganic Chemistry and Chemical Biology | A7149
Van Vranken & Weiss | 978-0-8153-4214-4
Answer 7.8
© www.garlandscience.com design by www.blink.biz
is
Th




OH
B HO B B ‡
.. H H
H O - R R
O OR' O
.. O
HO HO HO
HO O OH HO O HOO O H
O H O H H
H AcHN H AcHN H AcHN sp2
sh




O O O
UDP•Mg UDP•Mg UDP•Mg



OH
HO
HO
O O O
O O OR'
H AcHN OH




This study source was downloaded by 100000763811389 from CourseHero.com on 04-29-2021 03:50:20 GMT -05:00


https://www.coursehero.com/file/37863454/Answers-to-Chapter-7pdf/