3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o...

28
"%# %3 !$ OHC OH O 1) CH 3 ONa, CH 3 OH 2) HCl, CH 3 OH O OH H 3 CO OH O HO OH 1 2 3

Transcript of 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o...

Page 1: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

�������� �� "�%�# ����������� ��������%�3 �!�$

OHC OH

O1) CH3ONa, CH3OH

2) HCl, CH3OH

O

OHH3CO

OH O HO OH

1 2 3

Page 2: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

�������� ������� ����

2

OCH3O–H

O OH O

O–

OH

1) ������

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OH

OH

2) β-���������

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O

OH

HH

H H HO O

H+

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OH3CO

H

O

1

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OH

OH

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OH

1 2

OHOOH

HO

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OHOHOOH

HO

HO

OH3 4

O

OH

OHHO

HO

OH

5

O

NH2

OH

HO

HO

OH

6

O

N

OH

HO

HO

OH

AcH

O

OH

OH

HO

COOH

OH

O

N

OH

HO

HO

OHAc

H

O

OH

OH

HO

COOHOH

7 8 9 10

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OHO

OH

OH

HO

HO

OH

1 2

OHOOH

HO

HO

OHOHOOH

HO

HO

OH3 4

O

OH

OHHO

HO

OH

5

O

NH2

OH

HO

HO

OH

6

O

N

OH

HO

HO

OH

AcH

O

OH

OH

HO

COOH

OH

O

N

OH

HO

HO

OHAc

H

O

OH

OH

HO

COOHOH

7 8 9 10

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KA2>-B�@<

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OCH3OH

OHHO

HO

O OCH3

OH

OHHO

HO

OHOHHHHOOHHOH

COOHOHHHHOOHHOH

O

OHOH

OHHO

COOH

CuO Cu2O Ag A2O

OHOH

OH

OHHO

HO

1 2 3 4

5 6

987 10

OH OHH H

Page 6: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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COOHOHHHHOOHHOH

6OH

H

O

OHOH

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HO

OHCHO

OH

OHHO

HO

aldehyde

AgNO3

NH4OH

OHCOOH

OH

OHHO

HOAg9

α-D-gulcose

COOHOHHHHOOHHOH

6OH

H

O

OHOH

OHHO

HO

OHCHO

OH

OHHO

HO

aldehyde

CuO

NaOH

OHCOOH

OH

OHHO

HOCu2O8

α-D-gulcose

O

OCH3OH

OHHO

HO

O OCH3

OH

OHHO

HO

1 2

O

OHOH

OHHO

HO

OHCHO

OH

OHHO

HO

aldehyde

CH3OH, cat. H2SO4

OHOHHHHOOHHOH

OHOH

OH

OHHO

HO

45OH

H

O

OHOH

OHHO

HO

OH

OH

DHO

HO

aldehydeα-D-gulcose

NaBH4

CH3OH–H2O

Page 7: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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O

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H

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OH

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COOHOH

7 8 9 10

Page 8: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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ラクトース

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� � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

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OHO

–OOC

OO

NHAc

O

HO

HOO

OH

OH

–OOC

OOH

OHO

–OOC

OO

NHAc

O–O3SOHO

OOH

OH

–OOC

OOH

OSO3–

O

O

–OOCO

OH

NHSO3–

–O3SO

Page 12: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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OOH

OHO

–OOC

OO

NHAc

O

HO

HOO

OH

OH

–OOC

OOH

OHO

–OOC

OO

NHAc

O–O3SOHO

OOH

OH

–OOC

OOH

OSO3–

O

O

–OOCO

OH

NHSO3–

–O3SO

↑  6  または  6,  8  両方選択しても正解

Page 13: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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O OH

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P O–O

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PO

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diacylglycerol

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N+H3pKa1 1.92 pKa3 10.70pKa2 8.37

HS COO–

NH2

OH– OH––S COO–

NH2H+

HS COOH

N+H3 H+ H+

OH–

Page 24: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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COOH

N+H3

H2NCOOH

N+H3

H3+NH+

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H2NCOO–

N+H3

H2NH+

OH–

H+

OH–

pKa1 2.16

pKa2 9.06 pKa2 10.54

Page 25: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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N+H3pKa1 1.92 pKa3 10.70pKa2 8.37

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NH2

OH– OH––S COO–

NH2H+

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N+H3 H+ H+

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Page 26: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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–S COO–

NH2

HS COO–

NH2

H+

S COO–

N+H3

S–OOC

N+H3

H H S COO–

N+H3

S–OOC

N+H3

– 2H•

S–OOC

N+H3

SCOO–

N+H3

� ������

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NH2

OH– OH––S COO–

NH2H+

HS COOH

N+H3 H+ H+

OH–

�� +1 ±0 –1 -2�����

pI =1.92 + 8.37

2= 5.145

Page 27: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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COOH

N+H3

H2NCOOH

N+H3

H3+NH+

OH–

COO–

NH2

H2NCOO–

N+H3

H2NH+

OH–

H+

OH–

pKa1 2.16

pKa2 9.06 pKa2 10.54

HS COOH

NH3

Page 28: 3 ! $p.bunri-u.ac.jp/lab23/esumi/2014syoutesutomatome1.pdf · 3so ho o oh oh –ooc o oh oso3– o o ...

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±0 –1(等電点)

pI =9.06 + 10.54

2= 9.80

COOH

N+H3

H2NCOOH

N+H3

H3+NH+

OH–

COO–

NH2

H2NCOO–

N+H3

H2NH+

OH–

H+

OH–

pKa1 2.16

pKa2 9.06 pKa2 10.54

+2 +1

プラスに荷電している

COOH

N+H3

H3+N

COOH

N+H3

H2N