Introduction to Cell Wall & Membrane Glycoconjugatesrcarlson/cellwall.pdf · 2005. 1. 6. ·...

Introduction to Cell Wall & Introduction to Cell Wall & Membrane Membrane GlycoconjugatesGlycoconjugates

General Aspects of Bacterial Cell WallsGeneral Aspects of Bacterial Cell Walls

pentaglycine

The The peptidyglycanpeptidyglycan((mureinmurein))

GramGram--Positive Bacterial Cell WallsPositive Bacterial Cell Walls

GramGram--Negative Bacterial Cell WallsNegative Bacterial Cell Walls

GramGram--Negative Bacterial Cell WallsNegative Bacterial Cell Walls

EPS

CPSCPS

General Aspects of General Aspects of EucaryoticEucaryotic GlycoproteinsGlycoproteins

GlycoproteinsGlycoproteinsOO--LinkedLinkedNN--linkedlinked

ProteoglycansProteoglycansOO--LinkedLinked

CommunicationCommunicationSynchonySynchony of of myocytesmyocytes

Contact InhibitionContact Inhibitione.g.e.g. kidney cells, cancer kidney cells, cancer

cellscells

Molecular recognitionMolecular recognitione.g.e.g. extracellularextracellular matrixmatrix

OO--Linked Linked GlycoproteinsGlycoproteins

Commonly found in cell surface Commonly found in cell surface glycoproteinsglycoproteins and on and on mucinsmucins..

OO--Linked Linked GlycoproteinsGlycoproteins

Two motifs:Two motifs: (a.) (a.) glycosylationglycosylationof most of of most of extracellularextracellulardomain (also in domain (also in mucinsmucins), and ), and (b.) (b.) glycosylationglycosylation extracellularextracellularstem region.stem region.

NN--Linked Linked GlycoproteinsGlycoproteins

ProteoglycansProteoglycansLarge carbohydrate attached to a core protein.Large carbohydrate attached to a core protein.

The carbohydrates are known as The carbohydrates are known as glycosaminoglycansglycosaminoglycans..

Primarily located on the cell surface.Primarily located on the cell surface.

Have high viscosity, low compressibility.Have high viscosity, low compressibility.

Structural integrity, interStructural integrity, inter--cellular passageways, cellular passageways, lubricating fluids, shock absorbers.lubricating fluids, shock absorbers.

GlycosaminoglycansGlycosaminoglycans(all contain an amino sugar)(all contain an amino sugar)

O

HOH

HH

H

H

OOOH

-OOC

O

HNHAc

HH

H

H

OOH

OH

RR

O

HOH

H-OOC

H

H

OOOH

HO

HNHAc

HH

-O3SO

H

OH

OH

RR

GlcAGlcAGlcNAcGlcNAc

IdeAIdeAGalNAcGalNAc--44--sulfatesulfate

HyaluronatesHyaluronates: : synovialsynovialfluid, vitreous humor, fluid, vitreous humor, loose connective tissue.loose connective tissue.

DermatanDermatan sulfates: sulfates: skin, skin, blood vessels, heart blood vessels, heart valves.valves.

O

HOH

HH

H

H

OOOH

-OOCO

HNHAc

HH

-O3SO

H

OH

OH

RR

(OSO3)

GlcAGlcA GalNAcGalNAc--4 or 64 or 6--sulfatesulfate

-

CondroitinCondroitin sulfate: sulfate: cartilage, bone, heart cartilage, bone, heart valvesvalves

-

-

-

O

HNHSO3

HH

H

H

O

OSO3

R

O

O

OSO3

HOOC

H

H

OOH

H

R H

-

-

-

O

HNHSO3

HH

H

H

O

OSO3

R

O

O

OSO3

HH

H

H

OOH

OOC

R H

GlcAGlcA--22--sulfatesulfate

IdeAIdeA--22--sulfatesulfate

NN--SulfoSulfo--GlcNGlcN--66--sulfatesulfate

NN--SulfoSulfo--GlcNGlcN--66--sulfatesulfate

Heparin & Heparin & HeparanHeparansulfate: sulfate: lining of the lining of the arteries in lungs, liver, arteries in lungs, liver, and skin (heparin is more and skin (heparin is more sulfated than sulfated than heparanheparan).).

O

HNHAC

HH

H

H

OOHO

OSO3

R

O

HOH

HH

OH

H

OH

OH

R

-

GalGalGlcNAcGlcNAc--66--sulfatesulfate

KeratanKeratan sulfate: sulfate: cornea, cornea, bone, cartilage aggregated bone, cartilage aggregated with with chondroitinchondroitin sulfate.sulfate.

ProteoglycanProteoglycan ExamplesExamples

ProteinProtein--carbohydrate Linkagecarbohydrate Linkage

GlycolipidsGlycolipids

••CellCell--cell recognitioncell recognition••Development/differentiationDevelopment/differentiation••Tissue typingTissue typing••Blood Group AntigensBlood Group Antigens

SphingolipidsSphingolipidsH2C CH CH

CHHC

CH3

OH

NH3+

OH

H2C CH CHCH

HC

CH3

OH

NH

OH

R

OCH2 CH CH

CHHC

CH3

O NH

OH

R

O

O

HOH

HH

OH

H

OHH

OH

GalactocerebrosideGalactocerebrosideSphingosineSphingosine CeramideCeramide

Neutral Neutral glycosylceramidesglycosylceramides

CH2 CH CHCH

HC

CH3

R NH

OH

R

O

GanglioGanglio GgGg GalGalββ3GalNAc3GalNAcββ4Gal4Galββ4Glc4Glc--CerCerLactoLacto LcLc GalGalββ33GlcNAcGlcNAcββ33GalGalββ4Glc4Glc--CerCerNeolactoNeolacto nLcnLc GalGalββ4GalNAc4GalNAcββ3Gal3Galββ4Glc4Glc--CerCerGloboGlobo GbGb GalNAcGalNAcββ3Gal3Galαα44GalGalββ4Glc4Glc--CerCerIsogloboIsoglobo iGbiGb GalNAcGalNAcββ3Gal3Galαα33GalGalββ4Glc4Glc--CerCerMolluMollu MuMu GlcNAcGlcNAcββ2Man2Manαα3Man3Manββ4Glc4Glc--CerCerArthroArthro AtAt GalNAcGalNAcββ4GlcNAc4GlcNAcββ3Man3Manββ4Glc4Glc--CerCer

CeramideCeramide ((CerCer))

Acidic Acidic GlycosylceramidesGlycosylceramides ((GangliosidesGangliosides))

CH2 CH CHCH

HC

CH3

O NH

OH

R

O

O

HOH

HH

H

H

OHO

OHO

HOH

HH

O

H

OH

OHO

HNHAc

HH

OH

H

OH

OHO

HOH

HH

OH

H

OHH

OH

O

HOOC

H

H

H

AcHN

OHOH

OHHOH2C

GangliosideGanglioside GGM1aM1a

GlcGlcGalGal

GalNAcGalNAc

NeuNAcNeuNAc (SA)(SA)

GalGal

GalGal--GlcGlc--CerCer

GalGal--GlcGlc--CerCerSASA˩˩


SASA˩˩


SASA˩˩

SASA˩˩

GangliosideGanglioside Structures and Structures and BiosynthesisBiosynthesis

CMPCMP--SA CMPSA CMP CMPCMP--SA CMPSA CMP

CMPCMP--SA SA

CMPCMP

GalNAcGalNAc--GalGal--GlcGlc--CerCerSASA˩˩

GalGal--GalNAcGalNAc--GalGal--GlcGlc--CerCerSASA˩˩

GalGal--GalNAcGalNAc--GalGal--GlcGlc--CerCerSASA˩˩ SASA˩˩

GGM2M2

GGM1aM1a

GGD1aD1a

CMPCMP--SA SA

CMPCMP

UDPUDP--GalNAcGalNAc

UDPUDP

UDPUDP--GalGal

UDPUDP

aa--seriesseries


SASA˩˩


SASA˩˩


SASA˩˩GGD2D2

GGD1bD1b

GGT1bT1b

CMPCMP--SA SA

CMPCMP


UDPUDP

UDPUDP--GalGal

UDPUDP

bb--seriesseries


SASA˩˩

SASA˩˩


SASA˩˩

SASA˩˩


SASA˩˩

SASA˩˩

GGT2T2

GGT3T3

GGQ1cQ1c

CMPCMP--SA SA

CMPCMP


UDPUDP

UDPUDP--GalGal

UDPUDP

cc--seriesseries

GGM3M3 GGD3D3

GGT3T3

Introduction to Cell Wall & Membrane Glycoconjugatesrcarlson/cellwall.pdf · 2005. 1. 6. ·...

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