CH2On

1
???????? ?? ???????????

• ??? 3
• ???? ????
• ??? ??? ????????????

2
????? ????????????

• ????????????
• ???????? ?? ??????? ??? ????????
• ??
• ????? ?? ?? ??? ???????? ???? ?? ????? ???
  ??????? ?? ????.
• ????? ???????? ?????? ?? ????????????
• (CH2O)n

3
?? ???? ???? ??????????

• ???????????? ?? ?????? ????
• ?? ?? ???? ??????? ?? ????? ??? ???????? ?????
  ??? ???.
• ????? ?????????
• ?? ?????????? ????? ??????? ?????????? ?????
  ??????? ?? ???? ???????? ????????? ?? ?? ????
  ?????.
• ??? ?????????
• ???????? ???? ???? ??? ?? 20 ???? ??????????
  ?????.

4
????????????

• ???????? ?? ??????? ?? ??? ?? 2 ???? ?????????
• ???? ???? ???? ???? ????? ?? ?????? ?? ?? ?? ???
  ??? ?? ??????? ??????? ??????? ?????.
• ?? ??? ??????????
• ?????
• ????

5
?????? ????????????
6
????? ???????????? ?? ???? ????? ????

• Triose (aldotriose ketotriose)
• Tetrose (aldotetrose ketotetrose)
• Pentose (aldopentose ketopentose)
• Hexose (aldohexose ketohexose)
• Heptose (aldoheptose ketoheptose)

7
Aldohexose and Ketohexose
8
Aldopentoses
9
Monosaccharides have asymmetric (chiral) centers
10
Chiral Carbon
11
Stereoisomers (Enantiomers and Diasteromers)
12
More About Stereochemistry

• Enantiomers have nearly identical chemical
  properties but differ in a characteristic
  physical property, their interaction with plane
  polarised light.
• Interaction between biomolecules is
  stereospecific.

13
?? ??? ???? ???? ???? ????????? ????? ???????????
14
?? ?????? ?? n ???? Chiral ?? ????? n2 ??????
????? ????? ????.
15
????? ???? ????????? ????? ????????????? ?? ???
?????? ???? ?????

• ????? ?? ?? ???? ?? ???? ????? ??????? ????? ??
  ??? ???? ?????? ?? ??????? ????? ?? ?? ???? ?????
  ??????? ????
• ?????? L
• (????? ?????? ????? ?? ??? ???? ???? ???
• L-glyceraldehyde ??? ???? OH ??? ?? (
• ?????? D
• (????? ?????? ????? ?? ??? ???? ???? ???
• D-glyceraldehyde ???? OH ??? ????)

16
???? ???????? ? ???????? ???? ????????? D ?????.
17
?????? ????????? ????? D ?????????????? ?????
18
?????? ????????? ????? D ?????????????? ????
19
????? ????? Epimer
20
?? ???????? ???? aldotetroses ? ????
?????????????? ?? ????? ????? ???? 5 ?? ????? (??
????? ???? ???) ?????? ????? ????????? ????? ????
?? ????
21
????? ??? ?????? ????? ????? ????? ??? ??? ??????
? ???????? ?? ??????? ???

• ??? ???? ?? ?? ??? ??? ????? ?? ???? ????? ?????
  ????? ?? ???? ?? ????? ?????? ????? ?? ???
  ??????? ????.

22
????? ?? ??? ????? D-Glucose
23
Pyranoses and Furanoses
24
?? ?????? ??????? ?????????????? ?? ????? ????
???? (configuration) ??? ??? ??? ????
hemiacetal/hemiketal ?????? ???? ?????
anomer???? ?? ???.
25
?Conformational Formulas of Pyranoses
26
Monosaccharides are Reducing Agents
27
?? ?????????

• ?? ?? ?????????? ?? ????????????? O-glycosidic
  ????? ??? ???
• ????? ??????????? ??????? ???? ????????? ?? ???
  ?? ???? ??????? ??? ???? ????? ?? ???? ????? ??
  ????.
• ??? ????? ??????? ????? ?? ????? ?? ??? ?????
  (????? ????????????) ? ?? ???? (???? ?????????
  ??? ???) ???.

28
????? ??????
29
??? ???????????? ?????? ??????????? (reducing
sugar) ??????

• ?????????? ???? ??????? ?? ??? ???? ??? ??? ?? ??
  (?????? ?? ?? ??? ?????????? ?? ????? ??????) ???
  ?? ??? ??? ???? ?? ?? ??? ????? ?? ????? ???? ??
  ??????.
• ??????? ???? ??????? ????? ????? ????????? ??????
  ???? ??? ????? ?? ??? ??? ?? ??? ? ?? ????? ??
  ??? nonreducing ??????.
• ?? ????? ?????????? ?? ??? ?????????? ??????
  ?????? ?? ???? ??????? ???? ?? ?????? ??????????
  (reducing end) ????????.

30
Naming Disaccharides

• Give the configuration (a or ß) at the anomeric
  carbon joining the first monosaccharide unit (on
  the left) to the second.
• Name the nonreducing residue (insert furano or
  pyrano as applicable in the name).
• Indicate in paranthesis the 2 carbon atom joined
  by glycosidic bond, with an arrow connecting the
  two numbers.
• Name the second residue.

31
?? ?????????? ????

• ?????? ??? ??? ???.
• ??????? ???? ??? ?? ???? ?????? ????? ?? ??? ? ??
  ??? nonreducing ???. (????).
• ?? ?? ?????????? ???? ?????? ?????? glycosides
  ???? ?? ???.
• ??? ?????? ?? ??? ???? ?????? ????? ???? ??? ??
  ?? ??? ????? ???? ??????.

32
??? ?????????

• ???? ????????????? ????? ?? ????? ?????.
• ???????? ?? ??? ??????? ????? ?? ???? ????? ?? ??
  ???? glycans ?? ???? ??????.
• ?? ???? ??? ?????????? ????? ?????? ??? ?????? ?
  ??? ????????? ?? ???????? ?? ?? ?? ???? ?? ????
  ?? ?? ?????? ?? ????.
• ????? ??? ??????? ????? ?????.

33
?? ??? ??? ???????

• Homopolysaccharides
• Contain a single type of monomer
• Serve as fuel storage (e.g. starch/glycogen) or
  structural elements (e.g. cellulose/chitin)
• Heteropolysaccharides
• Contain two or more different kinds of monomer
• Provide extracellular support for organisms of
  all kingdom (e.g. peptidoglycan is composed in
  part of a heteropolysaccharide)

34
Homo- and heteropolysaccharides
35
??????

• ?? ?????? ? ????? ????? ?? ??????? ?????? ?????
  ??? ???.
• ?????? ?????? ??? ?? ??? ??????? ?? ??? ???? ??
  ??? ?? ?? ?????? ???.
• ?????????? ??????? ???? ??? ???? ? ??? ??????? ??
  100 ?????? ?? ????.

36
?????? ? ??????????
37
???????

• ??? ??????? ????? ?? ???? ??????? ?????? ???.
• ????? ??????????? ?? ?????????? ????? ?? ????? 4
  1a ?? ??????? ?? ????? ??? 6 1a ????? ???
  ???? ??? ???? ?? ?? ????? ???????? (???? ???????
  ?? 8 ?? 12 ????) ?? ?? ????.
• ???????? ????? ?? ?????? reducing ? ????? ?????
  ?????? nonreducing ?? ??? ???? ?? ???. ???????
  ??????? ?????? ???? ????? ??????? ?? ???? ???????
  ????? ????? ?? ?? ?? ?????? nonreducing ??? ??
  ?????.

38
??? ????? ?? ??? ?????? ??? ????? ??? ????
39
??? ?????? ???? ????? ???? ? ???? ???? ?? ???
???? ?? ?? ???? ??????
40
?????????

• ??? ?????????? ????????? ? ????? ????? ?? ??
  ??????? ??-????? ?? ????? 6 1a ????? ??? ???.
  ???? ????? ???? ??? ?? ????? 3 1a ????? ? ????
  ????? ???? ??? 2 1a ? 4 1a ??? ?? ?????.
• ?? ????????? ???? ??????? ????????? ????
• size exclusion chromatography ??????? ??? ???
• ???? ?????? ?? ???? ?????????? ?? ??? ??? ?????
  ?????? ???? ????? ???????? ??? ?? ????????? ???.

41
?????

• ?? ???? ???????? ?? ????????? ? ???? ??? ?? ??
  ?????? ????? ?????? ???? ??????.
• ????? ??? ?? ????? ????? ??? ? ???? ?????? ?????
  ???? ???.
• ????? ?? ?????? ??????? ??? ???? ???? ??? ?? ??
  10000 ?? 15000 ???? ??-????? ????? ??? ???.
• ????? ????? ?? ?????????? ? ??????? ??? ??? ?? ??
  ????? ????? ??? ??????? ????? ?? ??? ß ???. ??
  ??? ???? ???? ?????? ? ?????? ????? ????? ??
  ?????????? ? ??????? ?????? ???.

42
?????? ?????
43
?????

• ?? ?????? ??????? ??? ?? ?? ???????
  N-acetylglucosamine ?? ????? ß ????? ??? ???.
• ???? ????? ??????? ????? ? ????? ???????? ????
  ????????? ?? ????-2 ?? ?? ???? ???? ????? ???
  ???.
• ?????? ?????? ????? ????? ???? ???? ?????? ? ??
  ????? ??? ????? ?????? ????? ???? ?????? ?????
  ...???? ??????.
• ????? ??????? ??? ?? ????? ?????????? ??? ???????
  ?? ????? ???.

44
Chitin
45
???? ??? ??????????? ?? ?????? ????? ???????? ?
??????

• Peptidoglycan
• Agar

46
Peptidoglycan

• ??? ???? ?????? ??????? ?????????? ?? ?????????
  ??? ?? ?? ??????? ?????? N-acetylglucosamine ?
  N-acetylmuramic acid ??? ???? ????? 6 1a ?? ??
  ???? ??? ???? ????? ??? ???.
• ???????? ??? ??? ?? ?? ?????? ????? ???? ?????
  ??? ? ???? ???????? ???? ????? ???? ??? ???? ??
  ????. ?????? ???? ????? ????? ?? ???? ??????
  ????. ??????? ???? ?? ?????? ??????? ?? ????.

47
Peptidoglycan
48
Agar

• ???? ??????? ??????? ???? ???? ??????? ??
  ?????????? ????? ??? ???? ?????.
• ???? ????? ??????? ?????????? ??????? ????? ?? ??
  ??-???????? ? ?? ???? ?-????????? ?? ??? ???? 3 ?
  6 ???? ???? ????? ??? ???.
• ?? ??? ???? ????
• ?????? (????? ??? ?? ??? ??????? 120000)
• ?????????? (????? ???? ???)
• ?? ???? ???? ????? ?? ??? ???? ??? ?????? ? ??
  ???????? ?????? ? ?? ?????? ?????? ?? ???? ????
  ???? ??????? ??????? ??????? ?? ??? ??????????
  ??????? ??????.

49
?????? ??????
50
?????? ? ??? ???? ?? ??? ?????????