Exam (elaborations)

Introduction to Bioorganic Chemistry and Chemical Biology: Chapter 4 Answers

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Course
CHEM180 (CHEM180)

Institution
British Columbia Institute Of Technology (BCIT )

Answer 4.1 The bulky tert-butyl group has a strong equatorial preference, the following two conformations will be predominant. The anti isomer cannot hydrolyze through neighboring group participation; the syn isomer can hydrolyze through neighboring group participation. OCH3 -O P O O :O- anti ...

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introduction to bioorganic chemistry and chemical biology answers to chapter 4
answer 41 the bulky tert butyl group has a strong equatorial preference
the following two conformations will be predom

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Introduction to Bioorganic Chemistry and Chemical Biology 1

Answers to Chapter 4
(in-text & asterisked problems)

Answer 4.1
The bulky tert-butyl group has a strong equatorial preference, the following two
conformations will be predominant. The anti isomer cannot hydrolyze through
neighboring group participation; the syn isomer can hydrolyze through neighboring
group participation.

m
OCH3 OCH3

er as
-O
P -O
P
O O

co
O O
..

eH w
-O
:O -
anti syn

o.
Van Vranken & Weiss | 978-0-8153-4214-4
Answer 4.2
rs e
Introduction to Bioorganic Chemistry and Chemical Biology | A4096
ou urc
© www.garlandscience.com design by www.blink.biz
There are two plausible mechanisms that avoid expulsion of an anionic H2N– group.
Without some mechanistic data, you cannot predict which is the most likely.
o

H B
HO .. B: H O
aC s

NH2 NH3+
vi y re

N N
- N N
HO: NH2 R O- -O :O - O
R O- NH3+
H B NH
N N N
N N N N
ed d

H B ..
R O B: H O - O .. R O- R O R O
NH2 NH2
ar stu

N N
N N ..
R O- R O-
Introduction to Bioorganic Chemistry and Chemical Biology | A4097
Van Vranken & Weiss | 978-0-8153-4214-4
is

Answer 4.3
© www.garlandscience.com design by www.blink.biz
Th

A CU U
3' C U C G G GG C
C U G U C G 5' 3' C U C G G A
G CC U G U C G 5' 5'
5' G A G C CC UG C A C A G C 3'
AG 5' GA G C C GG AG A C A G C 3' 3'
UC
sh

stem loops "kissing complex"
Introduction to Bioorganic Chemistry and Chemical Biology | A4098
Van Vranken & Weiss | 978-0-8153-4214-4
© www.garlandscience.com design by www.blink.biz

This study source was downloaded by 100000763811389 from CourseHero.com on 04-29-2021 03:53:54 GMT -05:00

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, 2 Introduction to Bioorganic Chemistry and Chemical Biology: Answers to Chapter 4

Answer 4.4
The following figure shows the minimum free-energy structure from RNAfold and
GeneBee and the second-lowest energy structure from MC-fold (the lowest-energy
structure from MC-fold did not match).
G CU
A
U U
U C GG
C C
G G UG
3' A C GC U
C CA U G
CGG CUCC
A CG
5' G C C G A G G G
UA U G C C U A AA
G CA CGA
C G C U GA
U A
C G
A A
G U
U G
UG
Introduction to Bioorganic Chemistry and Chemical Biology | A4099
Van Vranken4.5
Answer & Weiss | 978-0-8153-4214-4
© www.garlandscience.com design by www.blink.biz

m
four types of base pairs: A•T, C•G, G•C, or T•A

er as
co
5' N N N N N N N N N N
four types of unpaired bases: A, C, G, or T

eH w
3' N N N N N N N N N
N

o.
rs e twelve types of mis-matches:
A•A, A•C, A•G, C•A, C•C, C•T, G•A, G•G, G•T, T•C, T•G, T•T
ou urc
Total possibilities = 47• 44• 12
= 411• 12
o
= 50,331,648
Introduction to Bioorganic Chemistry and Chemical Biology | A4100
aC s

Van Vranken & Weiss | 978-0-8153-4214-4
Answer 4.6
vi y re

© www.garlandscience.com design by www.blink.biz

RNA RNA RNA
O
.. -
O O -
RNA O O O O O O O
-O
.. O
O H :B N N N
ed d

CH3 CH3 .. CH
3
ar stu

H B

RNA RNA
is

-
O .. O
O O
O O H
Th

N+ N
CH3 CH3
H
sh

Introduction to Bioorganic Chemistry and Chemical Biology | A4101
Van Vranken & Weiss | 978-0-8153-4214-4
© www.garlandscience.com design by www.blink.biz

This study source was downloaded by 100000763811389 from CourseHero.com on 04-29-2021 03:53:54 GMT -05:00

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Exam (elaborations)

Introduction to Bioorganic Chemistry and Chemical Biology: Chapter 4 Answers

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