Advances in BioScience

Enantioselective synthesis of secondary alcohols plays an important role in pharmaceuticals, pheromones, flavors and fragrances, etc. Biocatalysts has unique characteristics when compared with chemical (homogeneous and heterogeneous) catalysts. The present work provides a list of various cultures used for deracemisation/stereoselective synthesis of various natural and synthetic secondary alcohols

Dalal, S.

Raghav, N.

 
*Corresponding author:   
Email: nraghav.chem@gmail.com. 
www.sospublication.co.in      Journal of Advanced Laboratory Research in Biology 
                                                                                        
                                                                                                                                         
 
We- together to save yourself society                           e-ISSN 0976-7614 
 
 
 
 
 
Fermentation Technology: Use of Various Cultures for Deracemisation of Secondary 
Alcohols 
 
S. Dalal1 and N. Raghav2* 
 
1Department of Biotechnology, Kurukshetra University, Kurukshetra-132119, Haryana, India. 
*2Department of Chemistry, Kurukshetra University, Kurukshetra-132119, Haryana, India. 
 
 
Abstract: Enantioselective synthesis of secondary alcohols plays an important role in pharmaceuticals, pheromones, 
flavors and fragrances, etc. Biocatalysts has unique characteristics when compared with chemical (homogeneous and 
heterogeneous) catalysts. The present work provides a list of various cultures used for deracemisation/stereoselective 
synthesis of various natural and synthetic secondary alcohols. 
 
Keywords: Biocatalyst, Enantioselective synthesis, Stereoselective synthesis, Deracemisation, Fermentation 
technology. 
 
 
1. Introduction 
 
Development of efficient methods for the synthesis 
of enantiomerically pure chiral compounds is of 
tremendous importance. It has been reported that in the 
year 2004, nine out of ten top drugs contained 
enantiomerically pure compounds [1]. The requirement 
of one of the stereospecific products is because it 
interacts with biological molecules that are highly 
specific in action. The requirement of enantiomerically 
pure chiral compounds is not only in the field of 
pharmaceutics, but also is of great importance in the 
field of flavor and aroma chemicals, agriculture and 
specialty materials [2].  
Over the past decades, biocatalysis have been 
recognized as a highly valuable tool for organic 
chemists and microbiologists to prepare 
enantiomerically pure molecules. Among the various 
strategies for the synthesis of chiral molecules, use of 
chiral catalysts is an important and efficient technique 
and in enzyme-catalyzed enantioselective synthesis, 
these biological catalysts are the recently used ones. In 
addition, biocatalysis is relatively a green technology, 
as enzyme-catalyzed reactions can be carried out in 
aqueous medium at ambient temperature and neutral pH 
under atmospheric pressure and extreme conditions are 
also not required thus energy is saved. Moreover, the 
by-products are also not formed and the reaction is 
proceeding at an extremely high rate, maybe up to the 
order of 1020 [3]. It has proven to be a useful 
technology for the chemical industry for the reactions 
not easily feasible in organic chemistry. These days, 
highly stereo-, regio- and chemoselective 
biotransformations result in economically attractive, 
environmentally acceptable and simplified 
manufacturing processes. Enzymes have been 
efficiently used for resolution of racemic mixtures, 
although might not have competed well with chemical 
methods in synthesis. Phenylethylamine and ibuprofen 
are commonly cited compounds prepared using 
enzyme-based chiral processes. The use of pure 
enzymes requires additional steps that may further 
complicate the situation, therefore; there is an emerging 
trend for the use of microbes as a whole for the 
synthesis of enantiomerically pure compounds. Though, 
the story of microbial biotransformation has been 
associated with mankind since long and dates back to 
around 2000 years BC for the production of vinegar. It 
is the oldest, best-known examples of oxidations carried 
out by microbes. Pasteur in 1958 was the first to 
demonstrate the microbial resolution of tartaric acid. 
Ammonium salt of tartaric acid was resolved with the 
Volume 1, Issue 2, October 2010 Original Article 
 
Deracemisation of Secondary Alcohols        Dalal and Raghav 
 
J. Adv. Lab. Res. Biol.                                                                                                                                                                                                                       135 
help of mold Penicillium glaucum. Pasteur’s 
investigation for the conversion of alcohol into vinegar, 
also confirmed by Brown was also reported back in the 
nineteenth century, where the causative organism was 
named Bacterium xylinum. 
 
2. Biocatalyst 
 
Biocatalysts differ from chemical catalysts in many 
positive ways, viz. selectivity (strict recognition of the 
substrate with very high enantio-, regio- and 
chemoselectivities); safety (since reaction conditions 
are mild, the solvent is water, while ethanol and 
glucose, etc. are used as hydrogen sources instead of 
explosive hydrogen gas); natural and environmentally 
usable (biocatalysts include: microorganisms, plants, 
animals or their isolated enzymes so can be easily 
decomposed in the environment after use). 
Commercially available biocatalysts are easily available 
or can be cultured easily, including baker’s yeast and 
the alcohol dehydrogenases from baker’s yeast, 
Thermoanaerobium brockii (TBADH), horse liver and 
the hydroxysteroid dehydrogenase from Pseudomonas 
testosterone and Bacillus sphaericus. 
Biocatalysts can perform a reduction in non-
aqueous solvents like ionic liquids, organic solvents 
like benzene, cyclodextrin and hydrophobic polymers 
as well. It can be used to control the enantioselectivities 
as well as to improve the system’s environmental 
friendliness. For example, the alcohol dehydrogenase 
from G. candidum was used in supercritical CO2 around 
100 atm and 35°C and found to catalyze the reduction 
of fluoroacetophenones. In some cases, there could be 
competing enzymes with different enantioselectivities, 
in such condition, an inhibitor of the unnecessary 
enzyme(s) like allyl bromide, ethyl chloroacetate, allyl 
alcohol, methyl vinyl ketone, sulfur compounds, Mg2+ 
and Ca2+ etc. could be used. 
 
3. Enantioselective Reductions 
 
Enantiomerically pure secondary alcohols are 
important intermediates for the synthesis of 
pharmaceuticals, agrochemicals, pheromones, flavors 
and fragrances, liquid crystals and chiral auxiliaries in 
asymmetric synthesis [4]. Enzymatic reductions also go 
via prologs rule [5], but there are incidences where anti 
pre logs product is formed [6]. The present study is a 
compendium of work carried out by combining 
sequential oxidation reductions by the use of microbes 
to access a range of secondary alcohols from racemates 
[Table 1]. 
 
Table 1. 
 
Microorganism / Cultures Reactions catalysed References 
Bacillus stearothermophilus, 
 
Yarrowia lipolytica 
R
O
R
OH  
 
, , Ph-R=
 
 
[7] & [8] 
Alcaligenes bronchisepticus, 
Streptococcus faecalis Ph COOH
OH
Ph COOH
OH
 
 
[9] 
Pseudomonas polycolor, 
Micrococcus freudenreichii Ph COOH
OH
Ph COOH
OH
 
 
[10] 
Byssochlamys fulva 
O
O
O O O
H
OH
O O
OH
H
 
[11] 
Rhodococcus erythropolis 
O O
H
OH
O O
OH
H
 
 
[12] 
N. asteroides, 
Candida parapsilosis 
 O O
H
OH
O O
OH
H
 
 
[13] 
Catharanthus roseus 
N
Ph
N
Ph
OH
 
 
[14] 
Candida parapsilosis 
OH
OH
OH
OH  
 
[15] 
Deracemisation of Secondary Alcohols        Dalal and Raghav 
 
J. Adv. Lab. Res. Biol.                                                                                                                                                                                                                       136 
Candida boidinii 
OH OHOH OHOH
 
[16] 
Corynespora cassiicola 
 
Candida and Pichia spps. 
OH
OH
OH
OH  
1,2-diols 
 
[17] & [18] 
Corynespora cassiicola 
OH OH
OHOH
 
[13] 
Geotrichum candidum 
R
O
R
OH  
R=Aryl gp 
 
[19] 
Various bacteria, fungi, and 
mammalian cultures Diterpenoids, triterpenoids, steroids and synthetic substrates [20] 
Nicotiana tabacum and 
Catharanthus roseus Camphorquinones → α-ketoalcohols [21] 
Nocardia pseudosporangifera 
 
Nocardia fusca 
OH OH
 
 
OH OH
 
 
[22] 
Rhizopus arrhizus Diarylketone → Diarylmethanol [23] 
 
4. Conclusion 
 
The production of single enantiomer of various 
intermediates is increasingly important in the 
pharmaceutical and other industries. Organic synthesis 
is one approach for the synthesis of single enantiomer, 
but the process may be more complicated. Use of 
biocatalysts provides another dimension for the 
synthesis of chiral compounds. The resulting 
advantages of two catalysts over chemical catalysis are 
stereo- and regioselectivity. Moreover, it is also an 
aspect of green chemistry, another emerging trend in 
synthetic chemistry to achieve environmentally friendly 
processes. Different classes of enzymes provide 
stereospecificity to different types of reactions, may it 
be the resolution of racemic compounds or in the 
asymmetric synthesis of enantiomerically rich chiral 
compounds. Oxidoreductases have been used in the 
synthesis of chiral alcohols. 
Recently, biological catalysts in the form of whole 
cells have also been shown to be extremely 
stereoselective in the synthesis of secondary alcohols. 
The reduction yield high regio- and stereoselectivity 
that is difficult to be achieved with chemical catalyst. 
The need is to identify the particular cultures that will 
be reaction specific. 
 
References  
 
[1]. Gröger, H. (2010). Enzyme‐Catalyzed 
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New York.  
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[5]. Prelog, V. (1964). Specification of the 
stereospecificity of some oxidoreductases by 
diamond lattice sections. Pure Appl. Chem., 9: 
119–130. 
[6]. Faber, K. (1997). Biotransformations in Organic 
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[7]. Fantin, G., Fogagnolo, M., Giovannini, P.P., 
Medici, A. & Pedrini, P. (1995). Combined 
microbial oxidation and reduction: a new 
approach to the highyield synthesis of homochiral 
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10.1016/0957-4166(95)00402-5. 
[8]. Fantin, G., Fogagnolo, M., Medici, A., Pedrini, P. 
& Fontana, S. (2000). Kinetic resolution of 
racemic secondary alcohols via oxidation with 
Yarrowia lipolytica strains. Tetrahedron: 
Asymmetry, 11(11): 2367–2373. doi: 
10.1016/S0957-4166(00)00185-3. 
[9]. Tsuchiya, S., Miyamoto, K. & Ohta, H. (1992). 
Highly efficient conversion of (±)-mandelic acid 
to its (R)-(−)-enantiomer by combination of 
enzyme-mediated oxidation and reduction. 
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10.1007/BF01027017. 
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[10]. Takahashi, E., Nakamichi, K. & Furui, M. (1995). 
R-(−)-mandelic acid production from racemic 
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[11]. Lanzilotta, R.P., Bradley, D.G. & McDonald, 
K.M. (1974). Microbial Reduction of Ketopantoyl 
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27(1): 130-134.  
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(1987). One-Step Microbial Conversion of a 
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(1987). Stereoselective enzymatic oxidation and 
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English

Fermentation Technology: Use of Various Cultures for Deracemisation of Secondary Alcohols

The present study was conducted in Pinus roxburghii forest in the District Tehri Garhwal of Uttarakhand State to assess the soil properties, forest species composition and volume along altitudinal gradients. The study revealed that the moisture content and water holding capacity of soil increased with increasing altitudes while bulk density (BD) reduced with increasing altitude. The higher proportion of soil texture was contributed of sand &gt; clay &gt; silt in each altitude. The soil pH of entire forest was acidic in nature. The soil organic carbon (SOC) and nitrogen increased with increasing altitude. Phosphorus and potassium has not shown any trend with altitude. The associated shrubs in Pinus roxburghii forest were Rhus parviflora, Carissa opaca, Berberis aristata, Lantana camara and Rubus ellipticus. The highest and lowest density of P. roxburghii was recorded in top and middle altitude respectively. The total basal cover (TBC) and volume of P. roxburghii was reduced with increasing altitude

Kumar, Sanjay

Kumar, Munesh

Sheikh, Mehraj A.

*Corresponding author:   
Email : muneshmzu@yahoo.com. 
www.sospublication.co.in      Journal of Advanced Laboratory Research in Biology 
                                                                                        
                                                                                                                                         
 
We- together to save yourself society                           e-ISSN 0976-7614 
 
 
 
 
 
Effect of Altitudes on Soil and Vegetation Characteristics of Pinus roxburghii Forest in 
Garhwal Himalaya 
 
Sanjay Kumar, Munesh Kumar* and Mehraj A. Sheikh 
 
*Department of Forestry, HNB Garhwal University, Srinagar (Garhwal), Uttarakhand, India. 
 
 
Abstract: The present study was conducted in Pinus roxburghii forest in the District Tehri Garhwal of Uttarakhand 
State to assess the soil properties, forest species composition and volume along altitudinal gradients. The study 
revealed that the moisture content and water holding capacity of soil increased with increasing altitudes while bulk 
density (BD) reduced with increasing altitude. The higher proportion of soil texture was contributed of sand > clay > 
silt in each altitude. The soil pH of entire forest was acidic in nature. The soil organic carbon (SOC) and nitrogen 
increased with increasing altitude. Phosphorus and potassium has not shown any trend with altitude. The associated 
shrubs in Pinus roxburghii forest were Rhus parviflora, Carissa opaca, Berberis aristata, Lantana camara and 
Rubus ellipticus. The highest and lowest density of P. roxburghii was recorded in top and middle altitude 
respectively. The total basal cover (TBC) and volume of P. roxburghii was reduced with increasing altitude. 
 
Keywords: Altitude, Soil and Vegetation, Pinus roxburghii. 
 
 
1. Introduction 
 
Vegetation is a key factor in determining the 
structure of any ecosystem. Within a plant community, 
it determines microclimate, energy budget, 
photosynthesis, water regimes, surface runoff and soil 
temperature (Tappeiner and Cernusca, 1996). The plant 
community in a region is a function of time and 
altitude, slope, latitude, aspect, rainfall and humidity 
also play an important role in the formation of plant 
communities and their composition (Kharkwal et al., 
2005).  
Quantitative analysis of vegetation helps in 
understanding the structure, composition and the tropic 
organization of any community. Species composition 
and diversity vary from one habitat to another within 
the communities exposing identical physiognomic 
characteristics (Nautiyal et al., 1999). 
The Garhwal Himalaya is one of the hot spots of 
biodiversity, situated in the western part of Central 
Himalaya. The wide altitudinal range and rapid change 
in altitudinal gradient even at small distances and high 
endemism make it interesting for studies (Singh et al., 
1992; Zobel and Singh, 1997). 
The vegetation diversity of forest ecosystems of 
Himalaya is influenced by topography, soil, climate and 
geographical location of the region. There is a great 
diversity in the floristic pattern due to altitudinal 
variation, and rainfall (Arora, 1995). 
The nature of soil profile, pH and nutrient cycling 
between the soils and trees are the important 
dimensions to determine the site quality. The vegetation 
influences the physicochemical properties of the soil to 
a great extent. It improves the soil structure, infiltration 
rate and WHC, Hydraulic conductivity and Aeration 
(Ilorker et al., 2001; Kumar et al., 2004). The large 
variation is soil vegetation due to their interaction and 
change in soil and vegetation characteristics with 
altitudes is commonly observed in the Himalayan 
forests. Thus, the hypothesis was made that; 1. How the 
altitudes affect the soil and vegetation with increasing 
altitudes, Therefore, the present study was taken in the 
Pinus roxburghii forest to understand, the effect of 
altitudes on soil and vegetation in Garhwal Himalaya. 
 
Volume 1, Issue 2, October 2010 Original Article 
 
Effect of Altitudes on Soil and Vegetation in Garhwal Himalaya          Kumar et al 
 
J. Adv. Lab. Res. Biol.                                                                                                                                                                                                         131 
2. Materials and Methods 
 
The study area was located at 1100 - 1500 meter 
above sea level in the District Tehri Garhwal, 
Uttarakhand. The soil characteristics were analyzed by 
collecting five samples from 0-30cm depth at each 
altitude of Pinus roxburghii forest. The moisture (%), 
water holding capacity (WHC) and texture (%) of soil 
were determined as the methods described by Misra 
(1968). Soil pH was measured with dynamic digital pH 
meter. Soil organic carbon (SOC) was determined by 
the partial oxidation method (Walkey and Black, 1934). 
Total nitrogen (N) was determined using Kjeldahl 
methods (Jackson, 1958) and phosphorus (P) and 
potassium (K) by flame photometer methods (Jackson, 
1958). 
The phytosociological studies were carried in the 
tree and shrub layers by using 10m x 10m quadrat. A 
total of 10 quadrats was placed along transect at each 
altitude. The size and number of quadrats were 
determined as per species area curve (Misra, 1968) and 
the running means methods (Kershaw, 1973). The 
phytosociological attributes were calculated; as per the 
method described by Mueller-Dombois and Ellenberg 
(1974). 
 
3. Results and Discussion 
 
3.1 Soil characteristics 
In the present study, three different altitudes of 
Pinus roxburghii forest were taken to assess soil 
nutrient status and its effect on species composition, 
structure and volume of P. roxburghii forest.  
Among the physical properties, the lowest amount 
of moisture was in lowest attitude which increased with 
increasing altitudes but bulk density has shown a 
reverse trend with moisture which reduced with 
increasing altitude (Fig. 1). The water holding capacity 
increased with the increasing altitudes (Fig. 2). The soil 
texture was contributed by the highest proportion of 
sand followed by clay and silt in each altitude (Fig. 3). 
 
 
 
Fig. 1. Moisture and bulk density at different altitude. 
 
 
 
Fig. 2. Moisture and water holding capacity at different altitude. 
 
 
  
Fig. 3. Soil texture at different altitude.  
 
Among the chemical characteristics of soil, pH of 
entire forest was acidic in nature. The soil organic 
carbon increased with increasing altitudes with the 
range from 0.15 ± 0.10% to 0.42 ± 0.16%. The nitrogen 
has also shown an increasing trend with the increasing 
altitudes (Fig. 4). The range value of phosphorus was 
from 24.07 ± 5.61 kg/ha (1300m) to 32.77 ± 18.02 
kg/ha (1100m) (Fig. 5), while a range value of 
potassium was from 159.04 ± 54.97 kg/ha (1100m) to 
203.09 ± 43.54 kg/ha (1300m) (Fig. 5). 
 
 
 
Fig. 4. Soil organic carbon and nitrogen at different altitude. 
 
 
Effect of Altitudes on Soil and Vegetation in Garhwal Himalaya          Kumar et al 
 
J. Adv. Lab. Res. Biol.                                                                                                                                                                                                         132 
 
 
Fig. 5. Phosphorus and potassium at different altitude. 
 
3.2 Species composition and structure 
In entire forest, Pinus roxburghii was main tree 
species. The lower perennial shrub stratum was 
composed of Rhus parviflora, Carissa opaca, Berberis 
aristata, Lantana camara and Rubus ellipticus. Each 
shrub species were found with the association of P. 
roxburghii throughout the season of a year. The highest 
density (590 ind/ha) of P. roxburghii was at the top 
altitude and lowest (440 ind/ha) in middle altitude 
(Table 1), while total basal cover (TBC) reduced with 
increasing altitudes (Fig. 6). The volume of pine also 
followed a similar trend as total basal cover (Fig. 6). 
Among the associate species of Pinus roxburghii forest, 
maximum frequency and density was 50% (Rhus 
parviflora and Berberis aristata) and 220 ind/ha 
(Carissa opaca and Berberis aristata) respectively at 
lower altitude (Table 1) while maximum frequency and 
density was recorded for Berberis aristata at middle 
and top altitudes (Table 1). 
 
4. Discussion 
 
The soil pH ranged from 6.30 ± 0.31 (1100m) to 
6.57 ± 2.19 (1300m). The acidic nature of the soil in 
Garhwal Himalayan forests has also been discussed by 
various workers (Bhandari et al., 2000; Kumar et al., 
2005; Sheikh et al., 2010). The soil organic carbon was 
increased with increasing altitudes might be due to 
higher amount of moisture percent, which is a good 
indicator of higher soil organic carbon (SOC) in the 
soil. The lower BD at top altitudes is good indication 
that soils has occupied coarser structure of organic 
matter and enriches the spaces by soil organic carbon. 
Nitrogen also increased with the altitude. Phosphorus 
and potassium has not shown any trend with altitude. 
The water holding capacity reduced by reducing 
altitudes because higher bulk density in lower altitude 
has less pore space in the soil. The correlation 
coefficient among physical and chemical properties of 
soil with altitudes is shown in Table 2 and Table 3 
respectively. 
 
 
 
Fig. 6. Total basal cover and volume at different altitude. 
 
5. Conclusion 
 
The study concludes that the increasing moisture 
content and water holding capacity of soil with 
increasing altitude and reducing total basal cover and 
the volume of Pinus roxburghii with increasing altitude 
might be due to low input of litter and its slow 
decomposition, which is suppressed by factors such as 
low temperature, which suppresses microbial activities 
at high altitude results in slow decomposition of litter. 
Therefore, sufficient moisture and water retaining 
capacity of the soil also could not be helpful for 
increasing basal cover and volume of Pinus roxburghii 
forest with increasing altitude. 
 
Table 1. Frequency (F) and density (D) of species in Pinus roxburghii forest. 
 
Species 
Altitude (meters) 
1100 1300 1500 
F (%) D (ind/ha) F (%) D (ind/ha) F (%) D (ind/ha) 
Pinus roxburghii 100 470 100 440 100 590 
Rhus parviflora 50 200 40 160 30 90 
Carissa opaca 30 220 30 110 40 120 
Berberis aristata 50 220 70 270 80 260 
Lantana camara 20 70 20 50 10 30 
Rubus ellipticus 20 80 30 120 20 80 
 
 
 
 
Effect of Altitudes on Soil and Vegetation in Garhwal Himalaya          Kumar et al 
 
J. Adv. Lab. Res. Biol.                                                                                                                                                                                                         133 
Table 2. Correlation coefficient among physical properties with altitude 
 
 Moisture (%) BD (g/cm3) WHC (%) Sand (%) Silt (%) 
BD (g/cm3) -0.950*     
WHC (%) 0.972* -0.997*    
Sand (%) -0.999* 0.960* -0.979*   
Silt (%) 0.782* -0.548* 0.612* -0.761*  
Clay (%) 0.995* -0.977* 0.991* -0.998* 0.713* 
(*Significant at 0.05 level of significance) 
 
Table 3. Correlation coefficient among chemical properties with altitude 
 
 
 pH SOC (%) N (%) P (Kg/ha) 
SOC (%) 0.115    
N (%) 0.115 1   
P (Kg/ha) -0.745* -0.748* -0.748*  
K (Kg/ha) 0.955* 0.405 0.405 -0.910* 
(*Significant at 0.05 level of significance) 
 
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Fermentation Technology: Use of Various Cultures for Deracemisation of Secondary Alcohols

Effect of Altitudes on Soil and Vegetation Characteristics of Pinus roxburghii Forest in Garhwal Himalaya

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