《糖生物学》课程教学课件（讲稿）03 Open chain and ring structures of monosaccharides

Open chain and ring structures ofmonosaccharides1

Open%chain%and%ring%structures%of% monosaccharides 1%

1. Aldoses and ketoses: openchain structuresEmpirical formula CH,O (hydrated carbon)Contain an oxygen atom attached to each carbonHighlyfunctionalizedCH2OHCHOLinear carbon chainC=O(CHOH)nAldehyde at C-1(CHOH)nCH2OHVarious secondary alcoholCH2OHaldosesAprimaryalcohol at theendketosesprimary alcohols at both endsKetone withinthechain

1.%Aldoses%and%ketoses:%open% chain%structures Empirical%formula%CH2O%(hydrated%carbon)% Contain%an%oxygen%atom%aBached%to%each%carbon% Highly%funcConalized% Linear%carbon%chain% Aldehyde%at%CF1% Various%secondary%alcohol% A%primary%alcohol%at%the%end% primary%alcohols%at%both%ends% Ketone%within%the%chain% 2%

CHOCHOCHOCHO(CHOH),(CHOH),CHOH(CHOH)CH20OHCH2OHCH2OHCH20HglyceraldehydetetrosepentosehexoseCHOCHO1111OHHHHOICH2OHCH2OH三CHOCHOC-OHHO-CCH2OHCH2OHD- or R-L- or S-3

3%

1.1 Erythrose and therosediastereomersenantiomersn CHOH groups, 2n stereoisomersconfigurationconformationeclipsedstaggeredZigzag drawingFischerprojection

1.1#Erythrose#and#therose 4% n%CHOH%groups,%2n%stereoisomers%

Newman projections:0=000HHH0=60°HHHHHHHHHHHHHHHSawhorse structures:HHHHHHHHHHHHHH-HHHHeclipsed,=00staggered,0=60skew, = anything else5

5%

OHOHCHOCHO1CHO2CHOHO-OHHOHHOHC3HO-OHOHOHCH2OHCH2OH4D-erythroseL-erythroseCHOOHOHCHO.-OHCHOCHOHO2HOH20HOHHO3OHOHCH,OHOHCH,OH4D-threoseL-threose1.2 Pentoses and hexoses6

6% 1.2#Pentoses#and#hexoses#

CHOCHOCHO-OHHO-OH-OHCH2OH-OHCH2OHCH2OHD-glyceraldehydeerythrosethreose1PENTOSESCHOCHOCHOCHO-OHHOHO--OH-OH-OHHOHO--OH-OH-OH-OHCH2OHCH2OHCH2OHCH2OHriboselyxosexylosearabinoseHEXOSESCHOCHOCHOCHOCHOCHOCHOCHOOH HO-OH HOHO-OHHO-OHHOOH-OH HO-OH-OHHOHO-OHHO--OHHO-OH-OH-OHHO-OH-OH-OH-OH-OH-OH-OH-OHCH2OHCH2OHCH2OHCH2OHCH2OHCH2OHCH2OHCH2OHgulosegalactoseallosemannoseidoseglucosealtrosetalose

7%

OHOHOHOHOHOHOHOH=.?ICHOCHOCHOCHOHOH2CHOH2CHOHHOH2C二-OHOHOHOHOHOHOHOHD-glucoseD-mannoseD-alloseD-altroseOHOHOHOHOHOHOHOH111171IIFCHOCHOCHOCHOHOH2CHOHCHOH2CHOHCOHOHOHOHOHOHOHOHD-taloseD-guloseD-idoseD-galactose8

8%

1.3 Other monosaccharidesOHOHOHCH2OHCHOHOHHOHOHOOHD-fructose2-deoxy-D-riboseOHOHOHOH1166CHOCHOH30H3COHOHOHOHL-rhamnoseL-fucose9

1.3#Other#monosaccharides 9%

2 Ring structure of monosaccharides2.1 Hemiacetals and lactols+MeOHH+ or 'OHROMeHOH10

2#Ring#structure#of#monosaccharides 2.1#Hemiacetals#and#lactols 10%