16- D-fructose-16-diphosphate derivatives and method for preparing the same

• Main Authors: JANG, I SEOP, NOH, MIN SU, YOO, JAE WON, LEE, EUN YEONG, NAM, CHUN JA, KIM, DEOK HUI, KIM, SU HYEON
• Format: Patent
• Language: English; Korean
• Published: 23.01.2003
• Edition: 7
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

PURPOSE: Provided is a method for producing a D-fructose-1,6-diphosphate derivative which is formed by ester bond of fatty acid to D-fructose-1,6-diphosphate to increase its penetration into the skin, and which is hydrolyzed by an enzyme in a body to show bioactivity of a D-fructose-1,6-diphosphate. CONSTITUTION: The D-fructose-1,6-diphosphate derivative is represented by the formula(I), wherein at least one of R1, R2 and R3 is -OCOR'; R' is hydrogen, C2-C24 linear or branched chain saturated alkyl or unsaturated alkyl, or hydroxy substituted C2-C24 linear or branched chain saturated alkyl or unsaturated alkyl; and M is hydrogen, alkali metal or alkali earth metal. The method for producing the D-fructose-1,6-diphosphate derivative comprises the steps of: (A) reaction of fatty acid with thionyl chloride in an organic solvent in the equivalent ratio of 1:1 to 1:1.3 at 0 to 10 deg. C for 1 to 2 hours to prepare acyl chloride of fatty acid; and (B) reaction of the acyl chloride of fatty acid of the step (A) with fructose-1,6-diphosphate in a mixed solvent of water and an organic solvent in the equivalent ratio of 1:1 to 3.3:1. 본 발명은 하기 일반식 (I)로 표시되는 프럭토스-1,6-디포스페이트 (D-fructose-1,6-diphosphate) 유도체 및 그의 제조방법에 관한 것으로, 더욱 상세하게는 프럭토스-1,6-디포스페이트에 지방산이 에스테르 결합으로 연결되어 있어 피부 흡수가 증진되고 생체내 효소에 의해 분해되어 프럭토스-1,6-디포스페이트의 생리활성을 나타낼 수 있는 프럭토스-1,6- 디포스페이트 (D-fructose-1,6-diphosphate) 유도체 및 그의 제조방법에 관한 것이다. [식중, R, R및 R중 적어도 하나는 -OCOR'이고, (식중, R'는 수소, 탄소수 2~24개의 직쇄 또는 분지쇄의 포화 알킬기 또는 불포화 알킬기, 또는 히드록시기로 치환된 탄소수 2~24개의 직쇄 또는 분지쇄의 포화 알킬기 또는 불포화 알킬기이다.) M은 수소, 알칼리 금속 또는 알칼리 토금속이다.]