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

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

  • 3

    OHC OH

    O1) CH3ONa, CH3OH

    2) HCl, CH3OH

    O

    OHH3CO

    OH O HO OH

    1 2 3

  • 2

    OCH3OH

    O OH O

    O

    OH

    1)

    H+

    O

    OH

    OH

    2) -

    H+H+ O

    O

    OH

    HH

    H H HO O

    H+

    H2OO O

    CH3OHO OH3CO

    H

    O

    1

  • 1 10 -D- -D- -D-

    O

    OH

    OH

    HO

    HO

    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

  • 1 10 -D- -D- -D-

    O

    OH

    OH

    HO

    HO

    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

  • -D-

    (II)

    2

    (2 )

    O

    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

  • -D-

    (II)

    2

    (2 )

    COOHOHHHHOOHHOH

    6OH

    H

    O

    OHOH

    OHHO

    HO

    OHCHO

    OH

    OHHO

    HO

    aldehyde

    AgNO3

    NH4OH

    OHCOOH

    OH

    OHHO

    HOAg9

    -D-gulcose

    COOHOHHHHOOHHOH

    6OH

    H

    O

    OHOH

    OHHO

    HO

    OHCHO

    OH

    OHHO

    HO

    aldehyde

    CuO

    NaOH

    OHCOOH

    OH

    OHHO

    HOCu2O8

    -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

    aldehyde-D-gulcose

    NaBH4CH3OHH2O

  • 0

    O

    OH

    OH

    HO

    HO

    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

  • O

    OH

    OHHO

    HO

    OH

    CHOOHHHHOHHOOHHOH5

    NaBH4OHHHHOHHOOHHOH

    OH

    OH

    OHHO

    OHHO

    HO

    OH

    OHHO

    OHHO

    HOHO

    OH

    OH

    OH

    OHHO

    180

  • O

    OH

    OHHOHO

    O

    OH

    OHO

    HOOH

    a

  • OOH

    OHO

    OOC

    OO

    NHAc

    O

    HO

    HOO

    OH

    OH

    OOC

    OOH

    OHO

    OOC

    OO

    NHAc

    OO3SOHO

    OOH

    OH

    OOC

    OOH

    OSO3

    O

    O

    OOCO

    OH

    NHSO3

    O3SO

  • OOH

    OHO

    OOC

    OO

    NHAc

    O

    HO

    HOO

    OH

    OH

    OOC

    OOH

    OHO

    OOC

    OO

    NHAc

    OO3SOHO

    OOH

    OH

    OOC

    OOH

    OSO3

    O

    O

    OOCO

    OH

    NHSO3

    O3SO

    6 6, 8

  • O OH

    OHHO

    HO

    OPOO

    OCHO HO O

    POO

    O

    OOPO

    O

    O

    OH

  • OO P OO

    O

    O

    OO

    O OO

    R1R2

    OO

    PO

    1

    Fischer

    H

    = L

    *3

    S

    R2R1

    O

    OH

    OO

    O OO

    R1R2

    OO

    PO

    1

    2

    3

    OO

    O OO

    R1R2

    OO

    PO

    1

    2

    3

    OH

    O

    OOHOH

    P OO

    O

    PO

    OO

    PLC

    OO

    O

    R1R2

    OO

    1

    2

    3

    O OOPO

    OH

    O

    OOHOH

    P OO

    O

    PO

    OOIP3

    diacylglycerol

  • HS COO

    N+H3pKa1 1.92 pKa3 10.70pKa2 8.37

    HS COO

    NH2

    OH OHS COO

    NH2H+

    HS COOH

    N+H3 H+ H+

    OH

  • COOH

    N+H3

    H2NCOOH

    N+H3

    H3+NH+

    OH

    COO

    NH2

    H2NCOO

    N+H3

    H2NH+

    OH

    H+

    OHpKa1 2.16

    pKa2 9.06 pKa2 10.54

  • HS COO

    N+H3pKa1 1.92 pKa3 10.70pKa2 8.37

    HS COO

    NH2

    OH OHS COO

    NH2H+

    HS COOH

    N+H3 H+ H+

    OH

    HS COOH

    NH2HO COOH

    NH2H H

    HS COOH

    NH2H

    SH

    HOOC

    NH2H

    90COOH

    H2N HSH

  • S COO

    NH2HS COO

    NH2H+

    S COO

    N+H3S

    OOC

    N+H3

    H H S COO

    N+H3S

    OOC

    N+H3

    2H

    SOOC

    N+H3S

    COO

    N+H3

    HS COO

    N+H3pKa1 1.92 pKa3 10.70pKa2 8.37

    HS COO

    NH2

    OH OHS COO

    NH2H+

    HS COOH

    N+H3 H+ H+

    OH

    +1 0 1 -2

    pI =1.92 + 8.37

    2= 5.145

  • COOH

    N+H3

    H2NCOOH

    N+H3

    H3+NH+

    OH

    COO

    NH2

    H2NCOO

    N+H3

    H2NH+

    OH

    H+

    OHpKa1 2.16

    pKa2 9.06 pKa2 10.54

    HS COOH

    NH3

  • 0 1

    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

    COOH

    N+H3

    H3+N

    COOH

    N+H3

    H2N