Chemoenzymatic Access to Chiral Tetrols Produced by Thiamine Diphosphate Dependent Benzaldehyde Lyase

Article abstract of DOI:10.1002/ejoc.201800980

Highly functionalized polyol building blocks have been synthesized by means of stereoselective chemoenzymatic C–C bond formation followed by stereoselective reduction. Catalysis by thiamine diphosphate (ThDP) dependent benzaldehyde lyase (BAL) with glyceraldehyde acetonide as acceptor substrate gave highly stereoenriched polyols such as (1S,2S,3R)-1-phenylbutane-1,2,3,4-tetrol (1), the 3,4-protected anti-1,2-diol 5, and the precursor of both compounds, 2-hydroxyketone 4.

Full text of DOI:10.1002/ejoc.201800980

A Journal of
Accepted Article
Title: Chemoenzymatic Access to Chiral Tetrols Produced by Thiamine
Diphosphate Dependent Benzaldehyde Lyase
Authors: Michael Müller, Damir Zecevic, Philipp Germer, Lydia Walter,
and Ekaterina Gauchenova
This manuscript has been accepted after peer review and appears as an
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the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201800980
Link to VoR: http://dx.doi.org/10.1002/ejoc.201800980
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European Journal of Organic Chemistry
10.1002/ejoc.201800980
COMMUNICATION
Chemoenzymatic Access to Chiral Tetrols Produced by Thiamine
Diphosphate Dependent Benzaldehyde Lyase
Damir Zecevic, Philipp Germer, Lydia Walter, Ekaterina Gauchenova, and Michael Müller*
Highly functionalized polyol building blocks have been synthesized by
means of stereoselective chemoenzymatic C–C bond formation
followed by stereoselective reduction. Catalysis by thiamine
diphosphate (ThDP) dependent benzaldehyde lyase (BAL) with
glyceraldehyde acetonide as acceptor substrate gave highly
stereoenriched polyols such as (1S,2S,3R)-1-phenylbutane-
1,2,3,4-tetrol (1), the 3,4-protected anti-1,2-diol 5, and the precursor
of both compounds, 2-hydroxyketone 4.
Enzymes are powerful tools for (stereo)selective transformations
in an atom economic fashion resulting often in environmentally
friendly biocatalytic processes. Moreover, application of enzymes
opens new synthetic strategies, especially for the access to highly
functionalized and stereodefined compounds. The 1,2,3,4-tetrol
motif is found in a variety of bioactive compounds and in
organocatalyst ligands used for asymmetric synthesis
Scheme 1. Chiral 1,2,3,4-tetrols as the core structure of natural products (e.g.,
styryllactone[4–6] and the side chain of hopanoids[1–3]) and of organocatalysts
(
Scheme 1). A typical example for natural compounds is the side
(
e.g., TADDOL, a tetraaryl-disubstituted dioxolanedimethanol,[7,10] and cyclic
chain of hopanoids, which are described as structural equiva-
lents[1] of the sterols in prokaryotes.[2,3] Further, a masked tetrol is
phosphoric acids).[12]
the core structure of styryllactones, such as the goniofufurones,
goniopyrones, goniotriol, altholactone, and etharvensin.[4] Some
styryllactones are of interest from a pharmaceutical point of view,
due to their cytotoxic effects on human tumor cells.[5] The
Chiral tetrols, such as (1S,2S,3R)-1-phenylbutane-1,2,3,4-tetrol
(
1), can be accessed by means of desymmetrization of a meso-
silane.[
19]
However, this nine-step synthesis implements
challenging protective group chemistry and expensive chiral
catalysts. Here, we present a short and easy access to chiral tetrol
chemical synthesis of such polyols is usually a challenging
multistep process.[6] The tetrol moiety is also present in
organocatalysts such as the TADDOLs (tetraaryl-disubstituted
1
(Scheme 2) by means of a chemoenzymatic approach.
dioxolanedimethanols).[7]
A common chiral pool synthesis
strategy towards these catalysts starts from enantiopure tartaric
acid derivatives.[
8–11]
Chiral cyclic phosphoric acids, which are
accessible from chiral tetrols,[12] are considered powerful
organocatalysts for asymmetric reactions. Prominent examples
[
13]
[
14]
include asymmetric selective C–H activations,
Friedel–Crafts
reactions,[
15,16]
and hetero-Diels–Alder reactions.[17,18]
Scheme 2. (1S,2S,3R)-1-Phenylbutane-1,2,3,4-tetrol (1).
Thiamine diphosphate (ThDP) dependent benzaldehyde lyase
(
BAL) from Pseudomonas fluorescens catalyzes carboligase and
carbolyase reactions.[20,21] BAL is able to produce highly
enantioenriched 2-hydroxy ketones in high chemical yield,
however mostly of lipophilic character.[22,23] We envisaged the
synthesis of polyols, usually a domain of aldolases[24–26] and
transketolases,[27–29] by employing BAL in carboligase reactions.
Accordingly, we reasoned that 2,2-dimethyl-1,3-dioxolane-4-
carbaldehyde (glyceraldehyde acetonide, 3) should be suitable
for an enzyme-catalyzed access to tetrols.
Thus, (S)-3 was synthesized by oxidative cleavage[30] of
D. Zecevic, P. Germer, L. Walter, Dr. E. Gauchenova,
Prof. Dr. M. Müller
Institute of Pharmaceutical Sciences, University of Freiburg
Albertstrasse 25, 79104 Freiburg (Germany)
E-mail: michael.müller@pharmazie.uni-freiburg.de
gulonolactone acetonide with NaIO
whereas rac-3 was synthesized by Dess–Martin oxidation
glycerol acetonide (2) in the hydrophilic ionic liquid 1-butyl-3-
4 2 2 2
in H O/CH Cl (Scheme 3B),
[
31]
of
methylimidazolium tetrafluoroborate ([bmim]BF
4
) (Scheme 3A).[32]
Carbaldehyde (R)-3 is commercially available.
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European Journal of Organic Chemistry
10.1002/ejoc.201800980
COMMUNICATION
4 2
reduction of 2-hydroxy ketones, Zn(BH ) is a suitable reducing
agent;[34] the chelated transition state leading to erythro
compounds (anti) is much more favored than the transition state
leading to threo compounds (syn).[ Thus, reduction of 4 with
35]
4 2
Zn(BH ) resulted in the anti-diol 5 diastereoselectively, in good
yield (87%). According to NMR spectroscopy and GC-MS, only
one stereoisomer (anti-5) is formed.
When NaBH
4
was used for the reduction of 4, the reaction was
less diastereoselective.[ In this case, the hydride transfer led to
a 90:10 ratio of anti- and syn-1,2-diol 5 which can be differentiated
by their retention times upon GC-MS analysis. The corresponding
tetrol 1 is obtained by acid hydrolysis of the acetonide protecting
group. Deprotection of anti-5 was achieved in 90% yield (Scheme
5), with a >99:1 diastereomeric ratio of the target product tetrol 1.
Advantageously, removal of the acetonide group can be
performed together with the Zn(BH ) reduction step in a one-pot
34]
Scheme 3. A) Synthesis of acetonide rac-3 by Dess–Martin oxidation[31] of
glycerol acetonide (2) in 1-butyl-3-methylimidazolium tetrafluoroborate
(
[bmim]BF
4
).[32] B) Synthesis of (S)-3 by oxidative cleavage[30] of gulonolactone
4
2
acetonide.
process with an overall yield of 93% from 4.
Glyceraldehyde acetonide (rac-3) is a suitable acceptor substrate
in BAL catalysis.[33] With benzaldehyde as a donor substrate, the
protected enantiopure (R,R)-phenylbutanone 4 was obtained.
Moreover, BAL is able to perform a kinetic resolution of rac-3 with
a preference for the (R)-3 acceptor substrate (Scheme 4). The
moderate yield of 4 (18%) can be attributed to a competitive
benzoin condensation reaction catalyzed by BAL.[21] The
diastereomeric excess (de) of 4 was higher than 98%, according
to HPLC and NMR analysis.
4 2
Scheme 5. Zn(BH ) -mediated diastereoselective reduction of 4 to anti-diol 5
and acid-catalyzed deprotection to tetrol 1.
In summary, we have established a straightforward access to
chiral tetrol 1, which is usually obtained by tedious multistep
procedures. This highly diastereoselective (de >99%) tetrol
synthesis is performed in two reaction steps and is based on two
commodity chemicals, benzaldehyde and rac-3 or (R)-3.
Furthermore, by enhancing the substrate scope of BAL and other
ThDP-dependent enzymes to aldolase acceptors, such as
acetonide-protected aldohexoses,[36] long-chain sugar-like
compounds might be accessible.
Experimental Section
4 2
Preparation of Zn(BH ) solution
ZnCl
(5 mL) at room temperature. The suspension was added to a solution of
dried NaBH (200.5 mg, 5.3 mmol) in anhydrous diethyl ether (15 mL), and
2
(512.4 mg, 3.76 mmol) was suspended in anhydrous diethyl ether
Scheme 4. Kinetic resolution of rac-3 catalyzed by BAL.[33] Yield of 4: 18%;
ee >95%; de >98%.
4
was stirred for 2 d. The supernatant was used for the reduction step.
In further reactions, benzaldehyde was tested for conversion with
enantiopure (S)-3 and (R)-3. The gulonolactone acetonide
derived aldehyde (S)-3 was not converted at all by BAL, whereas
Synthesis of rac-glyceraldehyde acetonide (rac-3) by Dess–
Martin oxidation of glycerol acetonide (2)
(
R)-3 led to enantiopure 4 in 30% yield. Hence, (R,R)-2-hydroxy
ketone 4 was easily obtained in one step from rac-3 or (R)-3. After
elucidating the enzymatic access to 4, we focused on chemical
modification with the aim of establishing 4 and the follow-up
products 1 and 5 as new and versatile building blocks with up to
three stereocenters.
The advantage of the biocatalytic conversion of benzaldehyde
and (R)-3 is demonstrated by the straightforward access to chiral
tetrol 1 by reduction of the carbonyl group. For anti-selective
In a flame-dried reaction flask under nitrogen atmosphere, Dess–Martin
periodinane (890.7 mg, 2.1 mmol) was added to a solution of 2 (277.2 mg,
2
.1 mmol) in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF
.7 mL) at room temperature. After 4 h, the reaction mixture was extracted
SO
4
,
4
with diethyl ether (2 × 10 mL). The organic layer was dried over Na
2
4
and the solvent was removed under reduced pressure. Purification was
performed via Kugelrohr distillation (5 hPa, 45 °C). Yield: 202.4 mg (73%);
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European Journal of Organic Chemistry
10.1002/ejoc.201800980
COMMUNICATION
1H NMR (400 MHz, CDCl
dd, J=4.8, 8.8 Hz, 1H, CH
J=1.9, 4.8, 7.5 Hz, 1H, CH), 9.74 (d, J=1.9 Hz, 1H, CHO); IR:  [cm–1] =
986 (m, C=O), 1372 (m), 1258 (m), 1211 (m), 1153 (m), 1071 (s), 848
m); chiral-phase GC (Lipodex D): t = 3.66 min [(R)-3], 7.89 min [(S)-3].
): =1.44 (s, 3H, CH
), 1.50 (s, 3H, CH
), 4.12
(s, 3H, CH
), 1.48 (s, 3H, CH
), 2.08 (s, 1H, OH), 3.12 (s, 1H, OH), 3.86 (t,
3
3
3
3
3
(
2
), 4.20 (dd, J=7.5, 8.8 Hz, 1H, CH
2
), 4.40 (ddd,
J=4.74 Hz, 1H, CHOH), 3.94–4.01 (m, 1H, CH), 4.02–4.08 (m, 2H, CH
4.85 (d, J=5.74 Hz, 1H, Ar-CHOH), 7.32–7.45 (m, 5H, Ar-H); 13C NMR
(100.6 MHz, CDCl ): =25.3 (CH ), 26.6 (CH ), 66.4 (CH ), 74.6 (CHOH),
75.6 (CHOH), 76.6 (CH), 126.8 (Ar-CH), 128.2 (Ar-CH), 128.5 (Ar-CH);
GC-MS: t = 11.26 min (anti-diol).
2
),
2
3
3
3
2
(
R
R
Synthesis of (S)-glyceraldehyde acetonide [(S)-3] by oxidative
cleavage of gulonolactone acetonide
Synthesis of (1S,2S,3R)-1-phenylbutane-1,2,3,4-tetrol (1) based on 5
NaIO
M NaOH was added until pH 5.5 was reached and the suspension was
stirred for 2 h, then CH Cl (10 mL) was added. The mixture was allowed
4
(4.90 g, 23 mmol) was suspended in water (6 mL) at –5 to 0 °C. 3
Acetonide anti-5 (10 mg, 0.042 mmol) was dissolved in methanol (2 mL).
3 M HCl (1 mL) was added at room temperature (a higher concentration of
HCl leads to degradation of 5). After 1.5 h, the reaction was stopped by
adding diethyl ether (2 mL). The solvent was removed under reduced
pressure to give colorless, highly viscous tetrol 1. Yield: 7.53 mg (90%);
2
2
to warm to room temperature. Gulonolactone acetonide (1.82 g, 8.32
mmol) was added in portions and the reaction mixture was stirred for 30
min. At 20 °C, K
between 5 and 6. After 3 h, the reaction mixture was saturated with NaCl
approximately 6 g). The precipitate was filtered using a Büchner funnel
and the solid was washed with a mixture of NaCl solution and CH Cl (1:1).
The aqueous layer was extracted with ethyl acetate (10 mL). The
combined organic layers were dried over MgSO and the solvent was
2
CO
3
solution (15%) was added to ensure a pH value
1H NMR (400 MHz, DMSO-d
3.38 (dd, J=6.32, 11.14 Hz, 2H, CH
6
): =3.24 (dt, J=3.17, 6.73 Hz, 1H, CHOH),
2
OH), 3.54–3.60 (m, 1H, CHOH), 3.72
(
(br s, OH), 4.66 (d, J=5.36 Hz, 1H, Ar-CHOH), 7.17–7.23 (m, 1H, Ar-CH),
7.24–7.30 (m, 2H, Ar-CH), 7.34–7.39 (m, 2H, Ar-CH); 13C NMR (100.6
2
2
6 2
MHz, DMSO-d ): =63.6 (CH OH), 73.0 (CHOH), 74.2 (Ar-CHOH), 75.5
4
(CHOH), 126.9 (Ar-CH), 127.6 (Ar-CH), 128.2 (Ar-CH), 143.3 (Ar-C).
removed under reduced pressure (600 hPa, 40 °C). Purification was
performed via Kugelrohr distillation (5 hPa, 45 °C). Yield: 549.2 mg (50%).
Synthesis of (1S,2S,3R)-1-phenylbutane-1,2,3,4-tetrol (1) based on 4
in a one-pot process
Production of 2-hydroxy ketone 4 by enzymatic conversion of
benzaldehyde and (R)-3
2-Hydroxy ketone 4 (23 mg, 0.097 mmol) in anhydrous diethyl ether (2 mL)
was charged with Zn(BH
of the Zn(BH solution, the reaction temperature was slowly allowed to
warm to room temperature. After 5 h, another portion of Zn(BH solution
4 2
) solution (350 L) at –30 °C. After the addition
Modified literature procedure[33] (see the Supporting Information).
4 2
)
4 2
)
Synthesis of anti- and syn-diol 5 by using NaBH
4
(150 L) was added. The mixture was stirred for 24 h, then the reaction
was stopped by adding water (5 mL). The organic layer was charged with
3 M HCl (5 mL). The water of the aqueous layer was removed under
reduced pressure to obtain pure tetrol 1. Yield: 18 mg (93%).
NaBH
.04 mmol) in anhydrous diethyl ether (2 mL). After 8 h, the reaction was
stopped by adding water (5 mL). The organic layer was separated and
dried over Na SO . The solvent was removed under reduced pressure to
4
(1.9 mg, 0.05 mmol) was added to 2-hydroxy ketone 4 (9.5 mg,
0
2
4
give a mixture of anti- and syn-diol 5 as a colorless powder. Yield: 8.2 mg
Acknowledgements
1
(
85%); diastereomeric ratio: anti/syn, 90:10 (GC-MS); H NMR (400 MHz,
CDCl
3
): =1.38 (s, 3H, CH
3
), 1.48 (s, 3H, CH
3
), 2.08 (s, 1H, OH), 3.12 (s,
We thank Dr. Philippe Bisel (University of Freiburg) for critically
reading the manuscript and helpful comments, Dr. Kay Greenfield
for help in improving the manuscript, and the research group of
Prof. Dr. Martina Pohl (Forschungszentrum Jülich) for providing
the lyophilisate of benzaldehyde lyase from Pseudomonas
fluorescens.
1
4
H, OH), 3.86 (t, J=5.74 Hz, 1H, CHOH), 3.94–4.01 (m, 1H, CH), 4.02–
.08 (m, 2H, CH
2
), 4.85 (d, J=5.74 Hz, 1H, Ar-CHOH), 7.32–7.45 (m, 5H,
Ar-H); GC-MS: t
223 [M–CH
38), 105 (30), 91 (100), 77 (10), 55 (5).
R
= 11.26 min (anti-diol), 11.32 min (syn-diol); MS: m/z (%)
=
]+ (10), 203 (12), 178 (25), 160 (50), 145 (40), 133 (25), 118
3
(
Synthesis of anti-diol 5 by using Zn(BH
4
)
2
Keywords: • asymmetric biocatalysis • chirality •
diastereoselectivity • synthesis • polyols
2-Hydroxy ketone 4 (23 mg, 0.097 mmol) was dissolved anhydrous diethyl
ether (2 mL) and the mixture was added to Zn(BH
4
)
2
solution (350 L) at –
[1]
M. Rohmer, P. Bouvier-Nave, G. Ourisson, Microbiology 1984, 130,
1137–1150.
30 °C. The reaction mixture was slowly allowed to warm to room
[
[
2]
3]
B. Mycke, F. Narjes, W. Michaelis, Nature 1987, 326, 179–181.
N. Zhao, N. Berova, K. Nakanishi, M. Rohmer, P. Mougenot,
U. J. Jürgens, Tetrahedron 1996, 52, 2777–2788.
K. R. Prasad, S. L. Gholap, J. Org. Chem. 2008, 73, 2–11.
X.-P. Fang, J. E. Anderson, C.-J. Chang, P. E. Fanwick, J. L.
temperature. After 5 h, another portion of Zn(BH
4
)
2
solution (150 L) was
added. After 24 h, the reaction was stopped by adding water (5 mL). The
organic layer was separated and dried over Na SO . The solvent was
removed under reduced pressure. Yield: 20 mg (87%); diastereomeric
ratio: anti/syn-diol 5, >99:1 (GC-MS); 1H NMR (400 MHz, CDCl
): =1.38
2
4
[
4]
[5]
3
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European Journal of Organic Chemistry
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COMMUNICATION
McLaughlin, J. Chem. Soc., Perkin Trans. 1 1990, 1655–1661.
[23]
P. Dünkelmann, D. Kolter-Jung, A. Nitsche, A. S. Demir, P. Siegert,
B. Lingen, M. Baumann, M. Pohl, M. Müller, J. Am. Chem. Soc.
2002, 124, 12084–12085.
[
[
6]
7]
K. R. Prasad, S. L. Gholap, J. Org. Chem. 2008, 73, 2916–2919.
D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. Int. Ed. 2001,
4
0, 92–138.
[24]
[25]
W.-D. Fessner, V. Helaine, Curr. Opin. Biotechnol. 2001, 12,
574−586.
[
[
[
8]
M. Carmack, J. Org. Chem. 1968, 33, 2171–2173.
9]
H. B. Kagan, T. Dang, J. Am. Chem. Soc. 1972, 94, 6429–6433.
D. Seebach, H. Kalinowski, B. Bastani, G. Crass, H. Daum, H. Dörr,
N. P. DuPreez, V. Ehrig, W. Langer, C. Nüssler, H. Oei, M. Schmidt
Helv. Chim. Acta 1977, 60, 301–325.
P. Clapés, W.-D. Fessner, G. A. Sprenger, A. K. Samland, Curr.
Opin. Chem. Biol. 2010, 14, 154–167.
10]
[26]
[27]
P. Clapés, X. Garrabou, Adv. Synth. Catal. 2011, 353, 2263–2283.
G. Ali, T. Moreau, C. Forano, C. Mousty, V. Prevot, F. Charmantray,
L. Hecquet, ChemCatChem 2015, 7, 3163–3170.
C. Guérard-Hélaine, M. De Sousa Lopes Moreira, N. Touisni,
L. Hecquet, M. Lemaire, V. Hélaine, Adv. Synth. Catal. 2017, 359,
2061–2065.
[
[
[
11]
12]
13]
T. Budragchaa, A. Roller, M. Widhalm, Synthesis 2012, 44, 3238–
3
250.
X. Hu, R. Zhang, J. Xie, Z. Zhou, Z. Shan, Tetrahedron: Asymmetry
017, 28, 69–74.
D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014,
14, 9047–9153.
[28]
2
[29]
[30]
M. Pohl, C. Wechsler, M. Müller, Sci. Synth., Biocatal. Org. Synth.
2014, 93–126.
1
[
[
14]
15]
Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615–3618.
B. Bi, Q. Lou, Y. Ding, S. Chen, S. Zhang, W. Hu, J. Zhao, Org. Lett.
P. Bianchi, G. Roda, S. Riva, B. Danieli, A. Zabelinskaja-Mackova,
H. Griengl, Tetrahedron 2001, 57, 2213–2220.
D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155–4156.
J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. Venkat Narsaiah,
Tetrahedron 2004, 60, 2131–2135.
2
015, 17, 540–543.
K. Mori, M. Wakazawa, T. Akiyama, Chem. Sci. 2014, 5, 1799–
803.
[31]
[32]
[
[
[
16]
17]
18]
1
J. Pous, T. Courant, G. Bernadat, B. I. Iorga, F. Blanchard,
G. Masson, J. Am. Chem. Soc. 2015, 137, 11950–11953.
J. Zhao, S. Sun, S. He, Q. Wu, F. Shi, Angew. Chem. Int. Ed. 2015,
[33]
[34]
E. Janzen, M. Müller, D. Kolter-Jung, M. M. Kneen, M. J. McLeish,
M. Pohl, Bioorg. Chem. 2006, 34, 345–361.
S. M. Husain, T. Stillger, P. Dünkelmann, M. Lödige, L. Walter,
E. Breitling, M. Pohl, M. Bürchner, I. Krossing, M. Müller,
D. Romano, F. Molinari, Adv. Synth. Catal. 2011, 353, 2359–2362.
T. Nakata, T. Tanaka, T. Oishi, Tetrahedron Lett. 1983, 24, 2653–
2656.
54, 5460–5464.
[
[
[
19]
20]
21]
D. Liu, S. A. Kozmin, Angew. Chem. Int. Ed. 2001, 40, 4757–4759.
B. Gonzáles, R. Vicuña, J. Bacteriol. 1989, 171, 2401–2405.
A. S. Demir, M. Pohl, E. Janzen, M. Müller, J. Chem. Soc., Perkin
Trans. 1 2001, 633–635.
[35]
[36]
D. G. Gillingham, P. Stallforth, A. Adibekian, P. H. Seeberger,
D. Hilvert, Nat. Chem. 2010, 2, 102–105.
[
22]
A. S. Demir, Ö. Şeşenoglu, E. Eren, B. Hosrik, M. Pohl, E. Janzen,
D. Kolter, R. Feldmann, P. Dünkelmann, Adv. Synth. Catal. 2002,
344, 96–103.
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European Journal of Organic Chemistry
10.1002/ejoc.201800980
COMMUNICATION
COMMUNICATION
A straightforward access to chiral
tetrols by means of a chemoenzymatic
approach. This highly diastereo-
selective (de >99%) tetrol synthesis is
performed in two reaction steps and is
based on two commodity chemicals.
Enzyme catalysis*
Damir Zecevic, Philipp Germer, Lydia
Walter, Ekaterina Gauchenova, and
Michael Müller
Page No. – Page No.
Chemoenzymatic Access to Chiral
Tetrols Produced by Thiamine
Diphosphate Dependent
Benzaldehyde Lyase
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