1. Phosphate Ester Formation
Hydroxyl group + H3PO4 --> Phosphate Ester
Phosphate esters are important compounds in carbohydrate metabolism.

2. Phosphate ester formation
-D-glucose-1-phosphate
Sugar and phosphate combinations are the basis for
nucleotides involved in DNA / RNA,
energy carrying molecules (ADP & ATP),
and chemical messengers (cAMP)
Henna and  Glucose-6-phosphate dehydrogenase deficiency: Catherine Cartwright-Jones c 2004  Kent State University
Henna can cause a haemolytic crisis in G6PD deficient infants.  G6PD deficiency is an inherited condition, and any infant who is diagnosed with this condition MUST NOT have henna.  Henna can cause severe anemia in G6PD deficient infants by penetrating their thin, fragile skin of infants and causing oxidative haemolysis of their blood cells.
G6PD deficiency is a recessive x-chromosome sex-linked inheritable trait. If males have that trait on their x chromosome, they will be affected.  For females have the trait on one of their x chromosomes, they will not be affected.  If both of a female's x chromosomes are G6PD deficient, they will be affected.  Therefore, in populations that have G6PD deficient individuals, males will be twice as likely to be adversely affected by henna as females.  The populations that have this trait are mostly in the Middle East and North Africa. This may be why men rarely have henna, or have henna in small applications, while women have extensive and frequent henna in those regional traditions. 
The natural red tannin dye in henna is Lawsone (2-hydroxy-1,4 napthoquinone).  This is similar in structure to 1,4 napthoquinone, a naphthalene metabolite which strongly oxidizes G6PD deficient cells. Strong oxidants, such as are found in fava beans and naphthalene fumes (most commonly encountered in mothballs) cause similar haemolytic crisis in children, and in large amounts, can endanger G6PD deficient adults.
G-6-PD deficiency is an inheritable, X-linked recessive disorder whose primary effect is the reduction of the enzyme G-6-PD in red blood cells, causing destruction of the cells, called hemolysis. Ultimately, this hemolysis leads to anemia -- either acute hemolytic or a chronic spherocytic type. In the United States, many more black than white people have the disorder. Approximately 10-14% of the black male population is affected. The disorder may occasionally affect a black women to a mild degree (depending on their genetic inheritance).
People with the disorder are not normally anemic and display no evidence of the disease until the red blood cells are exposed to an oxidant or stress.

3. Amino Sugar Formation
Hydroxyl group is replaced by an amino group --> Aldosamine
Important in cartilage polysaccharides and red blood cell markers (ABO)
There are 3 important, naturally-occurring amino sugars.
In each the amino group is on C#2.

4. Amino sugar formation Glucosamine and hyaluronic acid
act as the backbone for the formation of proteoglycans
found in the structural matrix
of joints

5. Glycosidic bonds: R-OH + HO-R'  R-O-R' + H2O
The hydroxyl group and a hydroxyl group
of another sugar or other compound can join together,
splitting out water to form a glycosidic bond.
R-OH + HO-R'    R-O-R' + H2O
Acting hemiacetal
Acting as an alcohol
glycosidic linking helps form disaccharides,
oligosaccharides, and polysaccharides
from rings of monosaccharides

6. Disaccharide formation
oligosaccharides
not usually free, but covalently linked to protein or lipid "glycoconjugates"
mannose very common
usually very branched
modified sugars very common, especially w/ charges
mucins, proteoglycans
polysaccharides
energy storage - 1 large soluble molecule better than 1000's of small ones starches
amylose: glc's linked by a(1,4) bonds
chains form helices - open center
amylopectins: a(1,4) chains plus a(1,6) branches (~ residues)
more soluble, why?
glycogen:
like amylopectin but more branches (~ residues)
structure
cellulose: glc's linked by b(1,4) bonds
flat sheets, insoluble, why?
chitin: glcNAc linked by b(1,4) bonds
Alpha () or beta () describes
the –OH orientation on C #1.
The numbers represent the C # connections on the Haworth projection

7. Disaccharides
Formation of disaccharides is like glycoside formation (condensation rxn)
Monosaccharide + alcohol --> glycoside + H2O
Monosaccharide + monosaccharide --> disaccharide + H2O
Disaccharide glycosidic linkage Reducing? Human Digestion
Maltose (1-4) yes easily
Cellobiose (1-4) yes no
Lactose (1-4) yes usually
Sucrose (1-2) no yes

8. Common Disaccharides:
Sucrose: a-Glucose and b-Fructose
a, b (12) glycosidic linkage
Milk sugar:
galactose and glucose
connected
a(14) glycosidic linkage of 2 D-Glucose molecules

9. Polysaccharides (glycan)
Variations
Homopolysaccharides vs. Heteropolysaccharides
Length of chain
Type of Glycoside Linkage
Degree of Branching
Properties
NOT sweet
No positive Tollens or Fehling’s test
Limited water solubility
Colloids form readily

10. Storage Polysaccharides energy source (homopolysaccharides)
Starch (plants)
amylose (15-20%)
straight-chain
-glucose polymer
(~1000 G)
amylopectin (80-85%)
branched chain (~100,000 G)
glucose polymer
(~100,0000 G)
Starch + H2O --> glucose
Nutritional value
Glycogen (animals)
Highly branched
glucose polymer
(~1,000,000 G)
Glucose <==> Glycogen
(stored in liver
& muscle)

12. Cellulose

13. Structural Polysaccharides (homopolysaccharides)
Cellulose (cell wall)
straight chain -glucose
polymer
Chitin (exoskeleton)
N-acetyl amino derivative of glucose

14. Cotton and wood are primarily cellulose
(14) glycosidic bonds of two glucose rings
create linear but angled bonding.
Our enzymes cannot match
this bond angle structure
to hydrolyze cellulose into cellobiose subunits or break that down to glucose

15. Acidic Polysaccharides (heteropolysaccharides)
Hyaluronic acid
Joint lubricant
Heparin
Anticoagulant
Hyaluronic acid: heteropolysaccharide –
2 different glucose derivatives:
Glucuronic acid plus
N-acetyl-b-D-Glucosamine
Alternates b(13) and b(14) linkage
Acidic polysaccharides associated with the connective tissue of joints give hurdlers such as these the flexibility needed to accomplish their task.

16. Glycolipids & Glycoproteins
These form when glycosidic linkages connect monosaccharides with lipids &/or proteins.
Very important molecules for cell recognition processes

17. Dietary Considerations
A balanced diet ~ 60% carbohydrate
Simple carbs = mono & disaccharides
Complex carbs = polysaccharides
Starch
Cellulose
Natural vs. Refined Sugars
Natural: a mixture of sugar and other compounds
Refined: 100% sugar molecules
Glycemic effect: due to the rate of carbohydrate digestion
Glycemic index

18. Glycemic Index:
Measures the rate that specific carbohydrates are hydrolyzed into glucose.
Slow release of glucose into blood = good
Quick release of glucose into blood / overproduction of insulin = bad