L-Gulose
(Synonyms: 古洛糖) 目录号 : GC60988
A carbohydrate starting material
Cas No.:6027-89-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
L-Gulose is a carbohydrate starting material.1,2 It has been used as a starting material in the synthesis of L-nucleoside-based anti-HIV agents.
1.Woodyer, R.D., Christ, T.N., and Deweese, K.A.Single-step bioconversion for the preparation of L-gulose and L-galactoseCarbohydr. Res.345(3)363-368(2010) 2.Jeong, L.S., Schinazi, R.F., Beach, J.W., et al.Asymmetric synthesis and biological evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-oxathiolane-pyrimidine and -purine nucleosides as potential anti-HIV agentsJ. Med. Chem.36(2)181-195(1993)
| Cas No. | 6027-89-0 | SDF | |
| 别名 | 古洛糖 | ||
| Canonical SMILES | O=C[C@H]([C@H]([C@@H]([C@H](CO)O)O)O)O | ||
| 分子式 | C6H12O6 | 分子量 | 180.16 |
| 溶解度 | Water: 250 mg/mL (1387.66 mM) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.5506 mL | 27.7531 mL | 55.5062 mL |
| 5 mM | 1.1101 mL | 5.5506 mL | 11.1012 mL |
| 10 mM | 0.5551 mL | 2.7753 mL | 5.5506 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
A concise synthesis of L-Gulose and its C-6 derivatives
Bioorg Med Chem 2022 Nov 1;73:117029.PMID:36174449DOI:10.1016/j.bmc.2022.117029.
A convenient route for the preparation of L-Gulose and its C-6 derivatives starting from commercially available 2,3:5,6-diisopropylidene-d-mannofuranose via C-5 epimerization as the key step was developed. 1-O-Benzylation followed by regioselective hydrolysis of the 5,6-isopropylidene group furnished benzyl 2,3-isopropylidene-α-d-mannofuranoside, which was subjected upon regioselective one-pot 6-O-benzoylation and 5-O-mesylation, providing the corresponding 5-OMs-6-OBz derivative in excellent selectivity. Treatment of this mesylate compound with potassium t-butoxide to remove the benzoyl group followed by intramolecular SN2 inversion led to benzyl 5,6-anhydro-2,3-isopropylidene-β-l-gulofuranoside, which could undergo not only nucleophilic substitutions to open the epoxide ring to give various C-6 derivatives, but also acidic hydrolysis to yield 1,6-anhydro-β-l-gulopyranose for further transformation into l-gulopyranosyl pentaacetate.
Efficient whole-cell biosynthesis of L-Gulose by coupling mannitol-1-dehydrogenase with NADH oxidase
Enzyme Microb Technol 2021 Aug;148:109815.PMID:34116746DOI:10.1016/j.enzmictec.2021.109815.
L-Gulose is a rare aldohexose to serve as a building block for anticancer drug bleomycin and nucleoside-based antivirals. However, preparative inaccessibility and high cost have hindered its pharmaceutical application. Despite a regio- and stereo-selective enzymatic synthesis of L-Gulose from d-sorbitol using a variant of NAD+-dependent mannitol-1-dehydrogenase from Apium graveolens (mMDH) was explored, low efficiency and productivity caused by NADH accumulation or insufficient amount of NAD+ limited the practical utility of this process. In this study, a stable and efficient NADH oxidase from Bacillus cereus (bcNOX) was found to be more compatible with mMDH to recycle NAD+ in E. coli cells for L-Gulose biosynthesis. After a systematic optimization of the whole-cell system, efficient biosynthesis of L-Gulose was achieved. Starting with 70 g/L of readily available and cheap d-sorbitol resulted in a volumetric productivity of 5.5 g/L/d. This whole-cell approach enables practical, efficient and environmentally friendly biosynthesis of L-Gulose and exhibits the potential of becoming a biocatalytic strategy for various enzymatic oxidative transformations.
Biochemical synthesis of the medicinal sugar L-Gulose using fungal alditol oxidase
Biochem Biophys Res Commun 2021 Oct 20;575:85-89.PMID:34461440DOI:10.1016/j.bbrc.2021.08.061.
Some rare sugars can be potently medicinal, such as L-Gulose. In this study, we present a novel alditol oxidase (fAldOx) from the soil fungus Penicillium sp. KU-1, and its application for the effective production of L-Gulose. To the best of our knowledge, this is the first report of a successful direct conversion of d-sorbitol to L-Gulose. We further purified it to homogeneity with a ∼108-fold purification and an overall yield of 3.26%, and also determined the effectors of fAldOx. The enzyme possessed broad substrate specificity for alditols such as erythritol (kcat/KM, 355 m-1 s-1), thus implying that the effective production of multiple rare sugars for medicinal applications may be possible.
Single-step bioconversion for the preparation of L-Gulose and L-galactose
Carbohydr Res 2010 Feb 11;345(3):363-8.PMID:20034622DOI:10.1016/j.carres.2009.11.023.
Both carbohydrate monomers L-Gulose and L-galactose are rarely found in nature, but are of great importance in pharmacy R&D and manufacturing. A method for the production of L-Gulose and L-galactose is described that utilizes recombinant Escherichia coli harboring a unique mannitol dehydrogenase. The recombinant E. coli system was optimized by genetic manipulation and directed evolution of the recombinant protein to improve conversion. The resulting production process requires a single step, represents the first readily scalable system for the production of these sugars, is environmentally friendly, and utilizes inexpensive reagents, while producing L-galactose at 4.6 g L(-1)d(-1) and L-Gulose at 0.90 g L(-1)d(-1).
Synthesis of L-Gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses
Carbohydr Res 1990 Jul 15;202:33-47.PMID:2224894DOI:10.1016/0008-6215(90)84069-7.
Methyl 6-S-phenyl-6-thio-a-D-glucopyranoside, prepared in high yield from methyl a-D-glucopyranoside by the action of diphenyl disulfide and tributylphosphine in pyridine, was converted into 6-S-phenyl-6-thio-D-glucitol pentaacetate (7) by sequential hydrolysis, borohydride reduction, and acetylation. Oxidation of 7 with 3-chloroperoxybenzoic acid gave the corresponding S-epimeric sulfoxides, which underwent Pummerer rearrangement to 1-epimeric L-Gulose S-phenyl monothiohemiacetal hexaacetates. Boron trifluoride-catalyzed reaction of the latter with thiophenol gave the analogous diphenyl dithioacetal, whereas base-catalyzed methanolysis led to free L-Gulose. Treatment of 7 with N-chlorosuccinimide afforded 1-epimeric 1-chloro-1-S-phenyl-1-thio-L-gulitol pentaacetates, which were hydrolyzed to provide aldehydo-L-gulose pentaacetate. The same reaction sequences were performed with 6-S-phenyl-6-thio-D-galactose, synthesized in two steps from 1,2:3,4-di-O-isopropylidene-a-D-galactopyranose, furnishing ultimately L-galactose, its diphenyl dithioacetal pentaacetate, and aldehydo-L-galactose pentaacetate. Similar reaction sequences for the chain-terminal interchange of oxidation state in other omega-S-phenyl-omega-thioaldoses may prove useful for the preparation of less-common sugar derivatives.