biosynthesis lecture 1 - introduction to biosynthesis and pharmacognosy
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Biosynthesis & Pharmacognosy
CS407
Paraic James 18h
Peter Kenny 18h
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Introduction
Main Biosynthetic Pathways
Biosynthesis o Car!ohydrates "#$ucose%
Pyruate & 'cetate (ormation(atty 'cids
Prostag$andins
Shi)imate'mino 'cids
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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'$)a$oids
Mor*hine Biosynthesis
+uc$eotides
Pyrro$e Pigments
'romatic Po$y)etides
,er*enes
Steroids
-Mi.ed/ Pathways
P$ant Sources o rugs
($aanoids
S*ectrosco*ic ,echniues
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Boo)s2
Basic 3rganic Chemistry Part I
,edder5 +echata$5 Murray5 Carndu
3rganic Chemistry
I66(inar
+atura$ Products
J6Mann5 6S6aidson et. al.
Medicina$ +atura$ Products
P6ewic)
3rganic Chemistry o Bio$ogica$ Pathways
McMurry5 Beg$ey
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Biosynthesis
9 Synthesis !y -+ature/
Primary Meta!o$ites & Secondary Meta!o$ites
Proteins ,er*enes
Car!ohydrates Steroids
(atty 'cids '$)a$oids
+uc$eic 'cids "+' etc.%
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Pharmacognosy
-Pharma)on/ #ree) or-:#/
-gnosis/ #ree) or-K+3;
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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M'I+ BI3S=+,>
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Glucose
C6H12O6
>AC
3
C33> >AC
3
3>
Pyruic 'cid "CA%
Pyruate C>AC"3%C339
'cetic 'cid "C?%
'cetate C>AC33
9
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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A PI+CIP' S,',I+# M',
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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'cetate "C?% is a maor Bui$ding B$oc) or2
(',,= 'CIS
P3=K
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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'cetate is a$so used to ma)e Mea$onic 'cid "C%
>AC
3
3>
OHHOOC
>AC 3>
Mevalonic Acid
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Mea$onate is is used a !ui$ding !$oc) or2
,
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Pyruate "CA% com!ines with Car!ohydrate
to *roduce2
Shi)imic 'cid "C7%
C33>
3>
>3 OH
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Shi)imate is the *recursor or2
'3M',IC 'MI+3 'CIS
CI++'MIC 'CI
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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,here a num!er o routes to ormation o 'mino'cids6
'mino 'cids are im*ortant *recursors or2
'K'3IS
P:I+
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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C>A
OH
COOH
O3
>AC
3
C33>
>AC 39
O
14C $a!e$$ed 'cetate
6-Methylsalicylic Acid
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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a!e$$ed 'cetate *roides a$$ the Car!on in
9Methy$sa$icyc$ic 'cid
"a!e$ inishes u* on eery second Car!on in
a *redicta!$e manner%
Knowing where the $a!e$ was in the starting
materia$ we can *redict where it wi$$ !e in the
*roduct6
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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Pro!$ems2
iicu$t to synthesiDe $a!e$$ed *recursors
iicu$t to get good incor*oration o the
$a!e$ into $iing organisms
iicu$ties arise with -di$ution/ o the $a!e$
!y the un$a!e$$ed *oo$
:sua$$y on$y a sma$$ amount o *roduct and
diicu$t to esta!$ish e.act $ocation o the
$a!e$
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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'$so diicu$t to esta!$ish the e.act seuence
un$ess the *roducts can !e iso$ated at dierenttime intera$s
A B C
a!e$ wi$$ a**ear in B !eore a**earing in C
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8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy
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?6 :se '!norma$ -M:,'+,/ systems
B$oc) one ste* o the seuence e6g6 missing
enDyme wi$$ cause !ui$d9u* o the starting
materia$ "B% or that ste* and $ater com*ounds
wi$$ not !e ormed "C%6
A B C
X
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