Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing nitrogen-containing organic compound
Reexamination Certificate
1999-06-21
2001-02-06
Lilling, Herbert J. (Department: 1651)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing nitrogen-containing organic compound
C435S195000, C435S197000, C435S280000
Reexamination Certificate
active
06184008
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method for producing an optically active sphingoid compound.
2. Description of the Related Art
Optically active sphingoid compounds having optically active erythro amino alcohol moiety have been used in cosmetics and medical supplies for treatment of hair and skin or production intermediates thereof.
Conventionally, these compounds are extracted and separated mainly from epidermis tissue of animals such as cows and pigs, alternatively obtained by several synthetic steps. However, they are expensive and a stable supply thereof is difficult since the production amount is limited. Therefore, a further provision of a convenient method for producing the said compound has been desired.
SUMMARY OF THE INVENTION
An object of the present invention is to provide: a method for producing an optically active erythro sphingoid ester of the formula I:
wherein R
1
and R
2
may be the same or different and represent an aliphatic hydrocarbon having 7 to 31 carbon atoms which may be substituted by one or more hydroxyl groups, and
R
3
and R
4
may be the same or different and represent an acyl group having 1 to 7 carbon atoms,
which comprises:
allowing a racemic mixture comprising the optically active erythro sphingoid ester of the formula I as defined above and its enantiomer to contact with an esterase having the ability to selectively hydrolyze the said enantiomer of the optically active erythro sphingoid ester of the formula I to produce an optically active erythro sphingoid alcohol compound of the formula II:
wherein R
1
and R
2
have the same meaning as defined above, and
R
3
*, and R
4
* represent a hydrogen atom and an acyl group having 1 to 7 carbon atoms provided that R
3
* and R
4
* do not simultaneously represent an acyl group having 1 to 7 carbon atoms; and
recovering the optically active erythro sphingoid ester of the formula I.
DESCRIPTION OF THE PREFERRED EMBODIMENT
Next, a description will be made to the racemic mixture comprising the optically active erythro sphingoid ester compound of the formula I as defined above and its enantiomer represented by the formula II as defined above.
Examples of the aliphatic hydrocarbon having 7 to 31 carbon atoms which may he substituted by one or more hydroxyl groups, represented by R
1
and R
2
, for example, include:
a liner or branched alkyl group having 7 to 31 carbon atoms which may be substituted by one or more hydroxyl groups,
a liner or branched alkenyl group having 7 to 31 carbon atoms which has one or more double bonds and may be substituted by one or more hydroxyl groups, and the like.
A liner or branched alkyl group having 7 to 31 carbon atoms which may be substituted by one to three hydroxyl groups, a liner or branched alkenyl group having 7 to 31 carbon atoms which has one to three double bonds and may be substituted by one to three hydroxyl groups and the like, are preferred.
Among the aliphatic hydrocarbon having 7 to 31 carbon atoms which may be substituted by one or more hydroxyl groups, for R
1
and R
2
, the aliphatic hydrocarbon having 7 to 26 carbon atoms which may be substitiuted by one or more hydroxyl groups are preferred.
Specific examples of the above-described preferred alkyl or alkenyl groups include:
a heptyl group, tridecyl group, tetradecyl group, pentadecenyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, heneicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, tracontyl group, hentriacontyl group, 1-tridecenyl group, 1-tetradecenyl group, 1-pentadecenyl group, 1-hexadecenyl group, 1-heptadecenyl group, 1-octadecenyl group, 1-nonadecenyl group, 1-eicosenyl group, 1-hydroxytetradecyl group, 1-hydroxypentadecyl group, 1-hydroxthexadecyl group, 1-hydroxtheptadecyl group, 1-hydroxyoctadecyl group, 1-hydroxynondecyl group, 1-hydroxyeicosyl group, 1-hydroxtheneicosyl group, 1-hydroxydocosyl groun, 1-hydroxytricosyl group, 1-hydroxytetracosyl group, 1-hydroxypentacosyl group, 1-hydroxyhexacosyl group, 1-hydroxyheptacosyl group, 12-methyl-tridecyl group, 14-methy-1-pentadecenyl group, 14-methyl-heptadecyl group and the like
Examples of the acyl group having 1 to 7 carbon atoms for R
3
and R
4
include an alkylcarbonyl group having 2 to 7 carbon atoms and the like.
Specific examples of the acyl group include an acetyl group, propionyl group, butyryl group and the like.
An acetyl group is more preferred.
Specific examples of the racemic erythro sphingoid ester include:
N-heptadecanoyl-1,3-O,O-diacetyl-2-amino-4-hexadecene-1,3-diol,
N-heptadecanoyl-1,3-O,O-diacetyl-2-aminohexadecane-1,3-diol,
N-heptadecanoyl-1,3-O,O-diacetyl-2-amino-4-octadecene-1,3-diol,
N-heptadecanoyl-1,3-O,O-diacetyl-2-aminooctadecane-1,3,4-triol,
N-heptadecanoyl-1,3-O,O-diacetyl-2-aminoeicosane-1,3-diol,
N-heptadecanoyl-1,3-O,O-dibutyryl-2-aminoeicosane-1,3-diol,
N-heptadecanoyl-1,3-O,O-diacetyl-2-aminoheptacosane-1,3-diol,
N-octadecanoyl-1,3-O,O-diacetyl-2-amino-15-methylhexadecane-1,3-diol,
N-octadecanoyl-1,3-O,O-diacetyl-2-aminohexadecane-1,3-diol,
N-octadecanoyl-1,3-O,O-dibutyryl-2-aminohexadecane-1,3-diol,
N-octadecanoyl-1,3-O,O-diacetyl-2-amino-4-octadecence-1,3-diol,
N-octadecanoyl-1,3-O,O-diacetyl-2-aminooctadecane-1,3,4-triol,
N-octadecanoyl-1,3-O,O-diacetyl-2-aminoeicosane-1,3-diol,
N-octadecanoyl-1,3-O,O-dibutyryl-2-aminoheptacosane-1,3-diol,
N-2′-hydroxyoctadecanoyl-1,3-O,O-diacetyl-2-amino-15-methylhexadecane-1,3-diol,
N-2′-hydroxyhexadecanoyl-1,3-O,O-diacetyl-2-aminohexadecane-1,3-diol,
N-2′-hydroxyhexadecanoyl-1,3-O,O-dibutyryl-2-aminohexadecane-1,3-diol,
N-2′-hydroxyeicosanoyl-1,3-O,O-diacetyl-2-amino-4-octadecene-1,3-diol,
N-2′-hydroxyeicosanoyl-1,3-O,O-diacetyl-2-aminooctadecane-1,3,4-triol,
N-2′-hydroxytetracosanoyl-1,3-O,O-diacetyl-2-aminoeicosane-1,3-diol,
N-2′-hydroxyhexacosanoyl-1,3-O,O-dibutyryl-2-aminoheptacosane-1,3-diol,
N-docosanoyl-1,3-O,O-dibutyryl-2-amino-15-methyhexadecane-1,3-diol,
N-tetracosanoyl-1,3-O,O-diacetyl-2-aminohexadecane-1,3-diol,
N-hexacosanoyl-1,3-O,O-dibutyryl-2-aminohexadecane-1,3-diol,
N-methyloctadecanoyl-1,3-O,O-diacetyl-2-amino-4-octadecene-1,3-diol,
N-pentacosanoyl-1,3-O,O-diacetyl-2-amino-4-docosene-1,3-diol,
N-pentacosanoyl-1,3-O,O-diacetyl-2-amino-4-octadecene-1,3-diol,
N-pentacosanoyl-1,3-O,O-diacetyl-2-aminoeicosane-1,3-diol, and the like. These sphingoid esters can be obtained, for example, by a method disclosed by T. Kolter et al. (Tetrahedron, 50, p.13425(1994)).
The esterase includes an esterase, protease and the like in addition to a narrowly-defined lipase, and may be derived from animals such as hogs, human and the like, derived from plants such as ricinus and the like, or derived from microorganisms belonging to Aspergillus, Candida, Fusarium, Geotrichum, Mucor, Nocardia, Penicillium, Rhizopus, Saccharomyces, Acromobacter, Acinetobacter, Alcaligenes, Chromobacterium, Escherichia, Pseudomonas, Sphingomonas, Bacillus, Burkholderia, Moraxella, Lactobacillus, Staphylococcus, Serratia, Yarrowia and the like.
An esterase produced by a transformed host organism, into which an isolated gene of the esterase is introduced by using recombinant DNA technology, can be used in the present invention
As the host organism, an organism belonging to the same genus or a host organism belonging to the different genus can be used.
As a more specific example of the esterase, a protein having an amino acid sequence represented by SEQUENCE ID NO: 2 or a sequence in which one or more amino acids in the amino acid sequence are added, deleted or substituted, is listed.
SEQ ID NO:1 represents the DNA sequence coding for the amino acid sequence represented by SEQ ID No:2.
A microorganism (
E. coli
JM 109/pAL 612 strain) producing the protein having the amino acid sequence represented by SEQUENCE ID NO: 2 has been deposited as FERM-BP5740 (accepted date: Nov. 7, 1996) under the Budapest Treaty at the Ministry of International Trade and Indust
Ishii Takeshi
Mitsuda Satoshi
Ohta Hiromichi
Sugai Takeshi
Birch & Stewart Kolasch & Birch, LLP
Lilling Herbert J.
Sumitomo Chemical Company Ltd.
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