It is a description of alanine, how it is synthesized, comparison among five papers to discuss their experimental work, discussion about experimental work, and then the conclusion....

1. Presented by
KOMAL AROOSH
Roll no :- S2019140032
Session:- 2019-2021
Synthesis of Alanine
IN THE NAME OF ALLAH, THE BENIFICIENT THE MERCIFUL

2. Abstract
INTRODUCTION (Alanine)
Comparison of Experimental Work
Discussion
Conclusion
References
CONTENTS

3. The main purpose of the following research was to compare and
synthesized the alanine through different experimental works. Different
methods were used to synthesis the alanine such as synthesis of alanine
in Methanosarcina bakeri and Methanobacterium
thermoautotrophicum, by hydro formylation and hydro carboxylation of
enamides, by template action of dissymmetric cobalt (III) complex, by
smooth brucella abortus and by hydrogenolytic asymmetric
transmination. Different substrates and catalysts were used as Schiff
bases were catalytically hydrogenated in methanol, ethanol, t- butanol,
tetrahydrofuran and benzene. The best method to synthesize the
alanine is the hydrogenolytic asymmetric transmination which yields 97
% of alanine while showing both R,S configuration.
Abstract

4. Alanine is a hydrophobic molecule
Alanine is amino propanoic acid.
Alanine is an non-essential amino acid.
Alanine is glucogenic amino acid.
INTRODUCTION

5. Alanine
STRUCTURE
The
average molecular
weight of alanine
is 89.09 g/mol.

6. NATURAL ALNAINE
S-Alanine
UNNATURAL ALNAINE
R-Alanine
ENANTIOMERS

7. Source Of
Energy
For muscles
and central
nervous
system
>Strengthens
the immune
system
>Breakdown
tryptophan
and vitamin B6
Helps to treat
diabetes
Helps to
prevent low
blood sugar
level
WHY DO WE NEED ALANINE?

8. from pyruvate
and branched
chain amino
acids
catalytical
reactions or by
degradation
of oxidative
deamination
FROM WHERE ALANINE
CAN BE SYNTHESIZED?

9. COMPARISON OF THE EXPERIMENTAL WORK
Temperature
Paper 1 Paper 2 Paper 3 Paper 4 Paper 5
34 oC 60 oC 37 oC 23 oC 23 oC

10. COMPARISON OF THE EXPERIMENTAL WORK
34 C
60 C
37 C
23 C 23 C
PAPER 1 PAPER 2 PAPER 3 PAPER 4 PAPER 5
Temperature
Temperature

11. COMPARISON OF THE EXPERIMENTAL WORK
Paper 1 Paper 2 Paper 3 Paper 4 Paper 5
Solvents Benzene/2-
Butanone
- Phenol-water
solvent
- MeOH, EtOH, t-
BuOH,PhH
Substrate N-vinylimides Methanosar
cina bakeri
Glutanic acid,Na
Pyruvate, Na4P2
O7, MnSO4
Cobalt III
complex
Ethyl Pyruvate and
ester
SOLVENTS
AND
SUBSTRATE

12. Configuration
Observed
R,S
Configuration
COMPARISON OF THE EXPERIMENTAL WORK

13. Physical Appearance
White
crystalline
solid
COMPARISON OF THE EXPERIMENTAL WORK

14. OPTICAL ROTATION
Synthesis of alanine was confirmed by the optical rotation.
Optical purities of alanine were obtained
by hydrogenolytic asymmetric
transamination (Paper 5)by using various
solvents MeOH, EtOH, t-BuOH, THF and
PhH, are 32.7 %, 24.6 %, 12.5 %, 7.58 %
and 2.28 % respectively.
In Paper 1 optical purity
noted was 88%.

15. Yield %age
Paper 1 Paper 2 Paper 3 Paper 4 Paper 5
59 % 32.3 % 18 % 61 % 97 %
COMPARISON OF THE EXPERIMENTAL WORK

16. 59%
32.30%
18%
61%
97%
0% 20% 40% 60% 80% 100% 120%
PAPER 1
PAPER 2
PAPER 3
PAPER 4
PAPER 5
Yield Percentage
COMPARISON OF THE EXPERIMENTAL WORK

17. • Paper 2 shows minimum time to synthesize the alanine but highest temperature.
• Paper 1 is showing lowest temperature in the synthesis of alanine.
• Optical purity in Paper 1 was highest while the yield percentage calculated in Paper
5 is highest.
According to the prices of solvents, substrate and catalysts involved Paper 2 may have
high rank on other papers but it required relatively high pressure.
DISCUSSION

18. Alanine has been synthesized from different methods.
According to all experimental work comparison we get that
Paper 5 is showing the best yield of 97 % at room
temperature, hence, the best synthesized method.
CONCLUSION

19. REFERENCES
• P1: Becker Y, Eisenstadt A , Stille J(1980)Asymmetric
Hydroformylation and hydrocarboxylation of Enamides.Synthesis of
Alanine and Proline. Journal of Organic Chemistry 45: 2145-2151
• P2: Kenealy W, Thompson T , Schubert K(1982) Ammonia
Assimilation and Synthesis of Alanine, Aspartate, and Glutamate in
Methanosarcina barkeri and Methanobacterium
thermoautotrophicum. Journal of Bactriology 150: 1357-1365
• P3. Altebern R, Housewright R (1951) Allanine synthesis and
carbohydrate oxidation by smooth brucelia abortus. Journal of
Bacteriology 62: 97-105
• P4. Asperger R, Liu C (1967) Asymmetric synthesis of alanine via
template action of dissymmetric cobalt (III) complex. Inorganic
Chemistry 6: 796-800
• P5. Harada K*, Katoka Y (1978) Asymmetric synthesis of alanine by
hydrogenolytic asymmetric transmination. Tetrahedron Letters 19:
2103-2106