Ligand Synthesi - Bryn Mawr College

Report
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….)

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