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Presented by
KOMAL AROOSH
Roll no :- S2019140032
Session:- 2019-2021
Synthesis of Alanine
IN THE NAME OF ALLAH, THE BENIFICIENT THE MERCIFUL
Abstract
INTRODUCTION (Alanine)
Comparison of Experimental Work
Discussion
Conclusion
References
CONTENTS
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
Alanine is a hydrophobic molecule
Alanine is amino propanoic acid.
Alanine is an non-essential amino acid.
Alanine is glucogenic amino acid.
INTRODUCTION
Alanine
STRUCTURE
The
average molecular
weight of alanine
is 89.09 g/mol.
NATURAL ALNAINE
S-Alanine
UNNATURAL ALNAINE
R-Alanine
ENANTIOMERS
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?
from pyruvate
and branched
chain amino
acids
catalytical
reactions or by
degradation
of oxidative
deamination
FROM WHERE ALANINE
CAN BE SYNTHESIZED?
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
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
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
Configuration
Observed
R,S
Configuration
COMPARISON OF THE EXPERIMENTAL WORK
Physical Appearance
White
crystalline
solid
COMPARISON OF THE EXPERIMENTAL WORK
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%.
Yield %age
Paper 1 Paper 2 Paper 3 Paper 4 Paper 5
59 % 32.3 % 18 % 61 % 97 %
COMPARISON OF THE EXPERIMENTAL WORK
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
• 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
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
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
Alanine review

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Alanine review

  • 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
  • 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
  • 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