The Two Bioinorganic Projects of Research Methodology Fall 2012
Pteridinyl
phenanthroline
Ligand Synthesis
Complex Synthesis
Biochemical
Studies
Tetraphenyl
porphyrin
Types of Pteridinyl Phenanthroline Ligands (and other)
DPPZ
L-allox
L-amino
L-keto
L-UN
Ligand Synthesis
(by Alexandra)
Pteridinyl phenanthroline synthesis
MeOH
20 h or so
in NaOH pH ~11
General Description of Ligand Synthesis
Group and Ligand Assignments for Synthesis and Characterization
Group #
Group 1 —
Group 2 —
Group 3 —
Group 4 —
Group 5 —
Group 6 —
Group 7—
‘Group’ 8 —
DPPZ
Students
ligand
complex
Linda Cho, Katie Guye
DPPZ
[Ru(bpy)2(DPPZ)](PF6)2
Rachael Kahlin,Julia Heer
L-allox
[Ru(bpy)2(L-allox)](PF6)2
Julie Han,Bingqing Li
L-amino
[Ru(bpy)2(L-amino)](PF6)2
Alicia Makepeace,Misha Sims
L-keto
[Ru(bpy)2(L-keto)](PF6)
Terry Huh,Maria Nam
L-keto
[Ru(bpy)2(L-keto)](PF6)2
Anna Kalinsky,Janielle Vidal
L-keto (to make L-aap)
[Ru(bpy)2(L-aap)](PF6)2
Chloe Baumann,Sara Kim
L-UN (to make L-alap)
[Ru(bpy)2(L-alap)](PF6)2
Alexandra Kirsch
L-tallox (thioalloxazine)
[Ru(bpy)2(L-tallox)](PF6)2
L-allox
L-amino
L-UN
L-keto
w/ Ru
L-aap
w/ Ru
L-alap
Group and Ligand Assignments for Synthesis and Characterization
Group #
Group 1 —
Group 2 —
Group 3 —
Group 4 —
Group 5 —
Group 6 —
Group 7—
‘Group’ 8 —
DPPZ
Phenylene
diamine
Students
ligand
complex
Linda Cho, Katie Guye
DPPZ
[Ru(bpy)2(DPPZ)](PF6)2
Rachael Kahlin,Julia Heer
L-allox
[Ru(bpy)2(L-allox)](PF6)2
Julie Han,Bingqing Li
L-amino
[Ru(bpy)2(L-amino)](PF6)2
Alicia Makepeace,Misha Sims
L-keto
[Ru(bpy)2(L-keto)](PF6)
Terry Huh,Maria Nam
L-keto
[Ru(bpy)2(L-keto)](PF6)2
Anna Kalinsky,Janielle Vidal
L-keto (to make L-aap)
[Ru(bpy)2(L-aap)](PF6)2
Chloe Baumann,Sara Kim
L-UN (to make L-alap)
[Ru(bpy)2(L-alap)](PF6)2
Alexandra Kirsch
L-tallox (thioalloxazine)
[Ru(bpy)2(L-tallox)](PF6)2
L-allox
5,6 –diamino
2,4 dihydroxy
pyrimidine
L-amino
4,5,6 –triamino
pyrimidine
L-keto
5,6 –diamino
4-hydroxy
pyrimidine
L-UN
5,6 –diamino
pyrimidine
True or false?
Blood is red because of the iron in hemoglobin.
“Red blood cells”
A close-up of red blood
cells within a capillary.
Over 99 percent
of the blood vessels in the body
are capillaries,
even though they only hold 5
percent of the body’s blood.
False
por·phy·rin
Function: noun
Etymology: from Greek porphyra purple
-any of various compounds with a macrocyclic structure that consists essentially of four
pyrrole rings joined by four =CH- groups; especially : one (as chlorophyll or hemoglobin)
containing a central metal atom and usually exhibiting biological activity
Nature’s synthesis of Porphyrin
the pyrrole ring is formed
Glycine
+
Succinyl CoA
Protoporphyrin IX
The Adler synthesis of simple, symmetrically substituted porphyrins:
Meso position
R = phenyl (TPP)
toluyl (TTP)
p-chlorophenyl (TClPP)
Ligand Synthesis: Condensations are a Theme
Schiff-Base Ligands
(Thanks, Eesha….)