Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1987-10-20
1990-08-28
Howard, Jacqueline V.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
C07C 4300, C07F 900
Patent
active
049527177
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to phosphoric acid esters of myoinositol and their salts as well as a preparation process thereof.
BACKGROUND ART
Inositol and phytic acid are contained in rice bran and have conventionally been used as food additives, etc. Substances, which are estimated as 1,4,5- and 2,4,5-tri-phospho-sn-myoinositols, have recently attracted attention as second messengers for intracellular translation or their metabolites. They have however been reported to exist only in very trace amounts in cells.
DISCLOSURE OF THE INVENTION
The present inventors have found a process for synthesizing many derivatives inclusive of di-, tri-, tetra- and penta-sn-myoinositol derivatives by using myoinositol or iditol as a starting material. These derivatives include many novel substances.
Inositol contains six hydroxyl groups. Phosphorylation of inositol is believed to result in the formation of 6 types of (mono)phospho-myoinositols (hereinafter abbreviated as "IP.sub.1 ") with phosphoric acid introduced in one of the hydroxyl groups, 15 types of IP.sub.2 with two phosphoric acid residual groups, 20 types of IP.sub.3 with three phosphoric acid residual groups, 15 types of IP.sub.4 with four phosphoric acid residual groups and 6 types of IP.sub.5 with five phosphoric acid groups.
Namely, the present invention provides a myoinositol derivative represented by the general formula (I): ##STR2## wherein S.sup.1 -S.sup.6 mean individually an alkyl group, an alkylene group, an aralkyl group, an aryl group, ##STR3## [R.sup.7 -R.sup.12 : alkyl group, aryl group, alkylene group, aralkyl group, hydrogen atom, metal.sup..sym., HNR.sub.3.sup..sym. or NR.sup..sym., and when either two of S.sup.1 -S.sup.6 have bonded to vicinal hydroxyl groups, they may be coupled together to form .dbd.CR.sup.12 R.sup.13, .dbd.CR.sup.12 OR.sup.13, .dbd.SiR.sup.12 R.sup.13, --SiR.sup.12 R.sup.13 OSiR.sup.12 R.sup.13 --, .dbd.BR.sup.12, .dbd.SnR.sup.12 R.sup.13, ##STR4## --P(OOH)--O--P(OOH)--(R.sup.12, R.sup.13 : alkyl, alkylenearyl, aralkyl or polymethylene in which both terminals of R.sup.12 R.sup.13 are connected together).
The present invention also provides a process for the preparation of a myoinositol derivative by causing a phosphorylating agent to act on a myoinositol derivative, which has been substituted with catalytic reduction removable substituent groups at the positions other than those to be substituted by phosphoric acid residual groups, and reducing the resulting myoinositol derivative catalytically.
An exemplary preparation process of myoinositol according to the present invention is a process for preparing myoinositol derivatives in accordance with which 1,4,5-tri-phopho-myoinositol is prepared by:
substituting the 4,5-positions of a myoinositol derivative, which has a bridge-type protecting group at the 1,2-positions thereof and catalytic reduction removable protecting groups at the 3,6-positions thereof, or a mixture of the derivative and an enantiomer thereof, said bridge-type protecting group being , .dbd.CR.sup.12 R.sup.13, .dbd.CR.sup.12 OR.sup.13, .dbd.SiR.sup.12 R.sup.13, --SiR.sup.12 R.sup.13 OSiR.sup.12 R.sup.13 --, .dbd.BR.sup.12 or .dbd.SnR.sup.12 R.sup.13 in which R.sup.12 and R.sup.13 may individually be an alkyl, aralkyl or aryl group and may optionally be connected together at the terminals;
removing the bridge-type protecting group from the 1,2-positions;
introducing different substituent groups to the 1,2-positions;
removing the substituting groups from the 1,4,5-positions;
phosphorylating the 1,4,5-positions; and
removing the protecting groups from the 2,3,6 positions.
The present invention can prepare, selectively and in good yields, naturally-occurring phosphorylated myoinositols led by 1,4,5-triphospho-myoinositol having an important function in living bodies and phosphorylated inositol compounds which are unknown in the nature and are novel. The present invention also provides novel intermediates useful for obtaining phosphorylated inositol compounds which can be used as intended drugs
REFERENCES:
patent: 4735936 (1988-04-01), Siren
patent: 4777134 (1988-10-01), Siren
patent: 4797390 (1989-01-01), Siren et al.
Chem. Abst., vol. 90, No. 3, Jan. 15, 1979, p. 694, Abst. No. 23455z, Zh. Org. Khim. 1978, 14(9), 1858-63 (Russ).
Chem. Abst., vol. 93, No. 9, 1 Sep. 1980, p. 673, Abstract No. 95518g, Zh. Org. Khim. 1980, 16(2), 315-22 (Russ).
Awaya Akira
Ishizuka Yusaku
Ozaki Shoichiro
Watanabe Yutaka
Howard Jacqueline V.
Mitsui Toatsu Chemicals Incorporated
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