Ajinomoto Co., Ltd.

Yutaka Honda

Kunisuke Izawa

Takayuki Suzuki

Masakazu Nakazawa

Hiroshi Shiragami

Satoshi Katayama

Naoko Kanno

Masayuki Arai

Hisao Iwagami

Eiichiro Suzuki

Tsutomu Harada

Keigo Shima

Takashi Nakano

Takahiro Sato

Yasuhiro Tanaka

Tomoyuki Onishi

Toshihide Yukawa

Satoji Takahashi

Naoko Hirose

Yasuyuki Otake

Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.

Process for producing 3-amino-2-oxo-1-halogenopropane derivatives

Method for producing epoxide crystal

A process for producing optically active amino acid derivatives having a cyclohexyl group or a substituted cyclohexyl group by hydrogenating an amino acid derivative containing an aromatic group in the presence of a ruthenium catalyst. The starting material may be an unprotected amino acid or an N- and/or C-protected derivative thereof. An major advantage of the process is that the reduction may be accomplished without substantial racemization.

Process for producing cyclohexylamino acids

Method for producing &agr;-hydroxy-&bgr;-aminocarboxylic acids

Compounds of the formula (1) ##STR1## wherein X and Y are each N or NH, Z is O or OH, (1) when X=N and Y=NH, Z=O, and *1 and *3 are double bonds, (2) when X=NH and Y=N, Z=O, and *2 and *3 are double bonds, (3) when X=N and Y=N, Z=OH, and *2 and *4 are double bonds, and R is a side chain derived from an amino acid; for example, the amino acid is glycine with R=H, alanine with R=CH.sub.3, glutamic acid with R=CH.sub.2 CH.sub.2 COOH, lysine with R=CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NH.sub.2, or leucine with R=CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3, and/or an analogues thereof are useful for imparting a 'thick, sour' taste to foods.

Seasoning material

The present invention provides a simple and inexpensive method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acids and their esters. An ester of an N-protected .alpha.-amino acid ester is converted into a .beta.-ketosulfoxide, which is then processed with an acid to give an .alpha.-ketohemimercaptal. Next, this is acylated and then processed with a base to obtain an N-protected .alpha.-acyloxy-.beta.-amino-thioester, which is then saponified to obtain an intended compound. According to the method of the present invention, it is possible to produce .alpha.-hydroxy-.beta.-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from a-amino acids. The method comprises reduced reaction steps, the selectivity in the method to give the intended product is high, and the yield of the product obtained is high.

Method for producing .alpha.-hydroxy-.beta.-aminocarboxylic acids

The present invention provides a simple and inexpensive method for producing a-hydroxy-.beta.-aminocarboxylic acids and their esters. An ester of an N-protected .alpha.-amino acid ester is converted into a .beta.-ketosulfoxide, which is then processed with an acid to give an .alpha.-ketohemimercaptal. Next, this is acylated and then processed with a base to obtain an N-protected .alpha.-acyloxy-.beta.-amino-thioester, which is then saponified to obtain an intended compound. According to the method of the present invention, it is possible to produce .alpha.-hydroxy-.beta.-aminocarboxylic acid derivatives, which are intermediates in producing various HIV protease inhibitors, renin inhibitors and carcinostatics, from a-amino acids. The method comprises reduced reaction steps, the selectivity in the method to give the intended product is high, and the yield of the product obtained is high.

.alpha.-acyloxy-.beta.-amino-thiocarboxylic acid esters

A seasoning composition containing food and an amino acid derivative that imparts a 'thick, sour taste' to the food.

A process for preparing 2',3'-dideoxyinosine comprising reducing a nucleoside of the formula IIIa or IIIb ##STR1## wherein R.sup.2 is hydrogen, C.sub.1-12 acyl, C.sub.1-12 alkyl, C.sub.7-8 aralkyl or a silyl protecting group; X is Cl, Br, or I; R.sub.5 is C.sub.1-12 acyl; H.sub.x is hypoxanthine; with hydrogen in the presence of a palladium catalyst; wherein said reduction is conducted in a solvent containing a base of pH 9-11 and wherein the solvent is acetonitrile, aqueous acetonitrile, aqueous ethyl acetate, or aqueous methanol.

Process for preparing 2', 3'- dideoxyinosine

A crude 2',3'-dideoxynucleoside compound is purified by extracting with an organic solvent, or crystallizing, the 2',3'-dideoxynucleoside compound from a basic aqueous solution having a pH of not less than 12 containing the same. In another embodiment of purification a basic aqueous solution having a pH of not less than 11 of a crude 2',3'-dideoxynucleoside derivative is brought into contact with a nonpolar porous resin, whereby the derivative is adsorbed on the resin, and then the thus adsorbed derivative is desorbed with an aqueous alcoholic solution. 2',3'-Dideoxynucleoside compounds which have utility as anti-AIDS drugs or anti-virus drugs can be isolated and purified in high purity and in high yield from their crude products containing impurities.

Method of purifying 2',3'-dideoxynucleosides

A process for preparing 2',3'-dideoxyadenosine of the formula ##STR1## wherein B is adenine, wherein R.sup.1 is hydrogen, C.sub.1-12 acyl, C.sub.1-12 alkyl, C.sub.7-8 aralkyl, or silyl, said process comprising:

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Kawasaki, Japan

Yutaka Honda