Sugar amino acids and oligosaccharide mimic prepared from sugar amino acids

A technology of sugar amino acids and simulants, which is applied in the field of sugar chemistry and can solve problems such as the difficulty in controlling glycosidic bonds

Inactive Publication Date: 2018-09-14
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As an important class of condensate molecules, oligosaccharides have been pursued by scientists for their unique biological properties. Although chemical synthesis and enzymatic methods have made some progress in the synthesis of oligosaccharides, the glycosidic bonds in the synthesis of oligosaccharides Control is still a very difficult thing

Method used

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  • Sugar amino acids and oligosaccharide mimic prepared from sugar amino acids
  • Sugar amino acids and oligosaccharide mimic prepared from sugar amino acids
  • Sugar amino acids and oligosaccharide mimic prepared from sugar amino acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthetic route of sugar block 1 (glucose-type sugar amino acid) is as follows:

[0054]

[0055] Reaction conditions a) (i) Ac 2 O,HClO 4 ; (ii) HBr-AcOH (33% w / w), CH 2 Cl 2 ; (iii) Zn, NaH 2 PO 4 ,H 2 O, acetone, 87.2% (three steps); b) (i) MeONa, MeOH; (ii) NaH, DMF, BnBr, 88.3%, (two steps); c) CH 3 NO 2 , CAN, KOH, MeOH; 47.8%; d)(i)H 2 ,10%Pd / C,MeOH; (ii)Boc 2 O,NaOH,MeOH / H 2 O(3:1), 63.5%, (two steps); e) TIPS, imidazole, DMF, 89.4%; f) BnBr, 18-crown-6, KOH, THF, 70.7%; g) TBAF, THF, 97.5 %; h) TEMPO, NaBr, TBABr, NaOCl; quan.; i) CH 3 I,NaHCO 3, DMF,quan..

[0056] Specific test operation and steps:

[0057] Compound 12: Add D-glucose (36.0g, 200mmol) and 140mL acetic anhydride to a 500mL round bottom flask, lower the reaction temperature to 0°C, stir well, add 4 drops of perchloric acid drop by drop, and slowly rise to room temperature, React for 30 minutes. After the complete reaction of the raw materials was monitored by TLC, the reac...

Embodiment 2

[0067] The synthetic optimization route of sugar building block 1 (glucose-type sugar amino acid) is as follows:

[0068]

[0069] Reaction conditions: a) ZnCl 2 , Ac 2 O / AcOH (2:1), 85.3%; b) MeONa, MeOH, 90.5%; c) (i) H 2 ,5%Pd / C,MeOH; (ii)Boc 2 O,NaOH,MeOH / H 2O(3:1),68.7%,(two steps); d)(i)LiAlH 4 ; THF; (ii) Boc 2 O,NaOH,MeOH / H 2 O(3:1), 63.5%, (two steps).

[0070] Specific test operation and steps:

[0071] Compound 20: The free radical addition product 14 (3g, 6mmol) was dissolved in 30mL of a mixed solution of acetic anhydride:acetic acid (2:1), and then at 0°C, the newly prepared anhydrous zinc chloride (7.5 -10eq) of 50mL acetic anhydride:acetic acid (2:1) solution was added to the reaction, the temperature was gradually raised to room temperature, and the reaction was carried out for 2h. After TLC monitors that the reaction of raw materials is complete, add 30mL water to the reaction, extract with dichloromethane (4×50mL), then wash with sodium bicarbona...

Embodiment 3

[0075] The synthetic optimization route of sugar block 5 (galactose-type sugar amino acid) is as follows:

[0076]

[0077] Reaction conditions: a) (i) Ac 2 O,HClO 4 ; (ii) HBr-AcOH (33% w / w), CH 2 Cl 2 ; (iii) Zn, NaH 2 PO 4 ,H 2 O, acetone, 78.3% (three steps); b) (i) MeONa, MeOH; (ii) NaH, DMF, BnBr, 76.7%, (two steps); c) CH 3 NO 2 , CAN, KOH, MeOH; 36.5%; d) ZnCl 2 , Ac 2 O / AcOH (2:1), 76.5%; e) (i) LiAlH4 ; THF; (ii) Boc 2 O,NaOH,MeOH / H 2 O(3:1),45.6%,(two steps).(f)TEMPO,NaBr,TBABr,NaOCl;quan.(g)CH 3 I,NaHCO 3 ,DMF,quan..

[0078] Specific test operation and steps:

[0079] Compound 22: Add D-galactose (20g, 111mmol) into a 500mL round-bottomed flask, then add acetic anhydride (80mL), put the reaction in an ice-water bath, lower the reaction temperature to 0°C, stir well and dropwise Add 3 drops of perchloric acid dropwise, and slowly rise to room temperature. After 30 minutes of reaction, the solution becomes clear. After TLC monitors that the reacti...

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Abstract

Belonging to the field of carbohydrate chemistry, the invention in particular relates to sugar amino acids and an oligosaccharide mimic prepared from the same. Cheap and easily available D-glucose andD-galactose are adopted as the starting raw materials for a series of reactions to obtain all-benzyl-protected glycal, the latter undergoes one-step free radical addition under the action of ceric ammonium nitrate (CAN) to obtain a precursor 2-C-nitro compound of SAAs, then Pd/C hydrogenation reaction for deprotection of Bn, reductive ammoniation and selective Boc protection reaction are carriedout to obtain a protected intermediate product of amino; then TIPSCl is utilized for selective protection of C-6 hydroxyl, then C-3 hydroxyl and C-4 hydroxyl are subjected to Bn protection, and deprotection of TIPS is carried out on C-6 hydroxyl; finally the C-6 hydroxyl is oxidized to obtain glucose-type and galactose-type SAAs blocks; and based on the obtained SAAs, a straight-chain type oligosaccharide mimic connected by an amido bond is synthesized, and condensation reaction is carried out to obtain 9 homologous and heterologous oligosaccharide mimics of straight-chain dimer, tetramer andoctamer. The method is simple, convenient, fast and effective.

Description

technical field [0001] The invention belongs to the field of sugar chemistry, and in particular relates to the design and synthesis of two novel sugar amino acids and three types of oligosaccharide mimics using them as monomers. The oligosaccharide mimics have a spatial structure that simulates polypeptide compounds. Background technique [0002] Sugar amino acids (SAAs) are a class of sugar derivatives containing both amino and carboxyl groups. Its structural features are: a class of multifunctional molecules with a pyranose ring or a furanose ring as the backbone, modified by carboxyl and amino groups, and possibly with a hydroxyl group. Due to the diversity of functional groups at its terminals, it provides organic chemists with a good opportunity to create structurally diverse natural analogs. Due to their special structural characteristics, SAAs not only have inherent pharmaceutical properties, but also can be used as building blocks for the preparation of modified bio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H7/02C07H1/00C08B37/00A61K31/702A61K31/7028A61K31/7012A61K31/715A61P43/00
CPCA61P43/00C07H1/00C07H7/02C08B37/006Y02P20/55
Inventor 胡静尹健田光宗
Owner JIANGNAN UNIV
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