Fructosyl-lysine
(Synonyms: 果糖-赖氨酸; Fructoselysine) 目录号 : GC60170
Fructosyl-lysine (Fructoselysine) 是葡萄糖与赖氨酸通过美拉德反应生成的一种氨基糖基化产物 (amadori glycation)。Fructosyl-lysine 是葡萄糖烷的前体，葡萄糖烷是一种赖氨酸-精氨酸蛋白交联物，可作为糖尿病中检测的指标。
Cas No.:21291-40-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fructosyl-lysine (Fructoselysine) is an amadori glycation product from the reaction of glucose and lysine by the Maillard reaction. Fructosyl-lysine is the precursor to glucosepane, a lysine-arginine protein cross-link that can be an indicator in diabetes detection[1].
Fructosyl-lysine (5 mM; 0.5 hours) catalyzes the ATP-dependent conversion of [14C]fructoselysine to anionic products suggesting the existence of a fructoselysine-kinase activity in E .coli extracts[2].Fructosyl-lysine (100 μM; 1 hour) contains a carbohydrate moiety and appears to be phosphorylated, it can be converted to glucose 6-phosphate in bacterial extracts in E .coli extracts[2].Fructosyl-lysine (25 mM; 25 hours) lets E. coli growth at a rate of about one-third of that observed with glucose as a carbon source. Lysine itself does not support growth in the absence of other carbon source and does not affect the growth observed with glucose[2].
Fructosyl-lysine and AGE residues is increased markedly in glomeruli, retina, sciatic nerve, and plasma protein in diabetic rats[1].
[1]. Rabbani N, et al. Hidden complexities in the measurement of fructosyl-lysine and advanced glycation end products for risk prediction of vascular complications of diabetes. Diabetes. 2015 Jan;64(1):9-11. [2]. Karachalias N, et al. Accumulation of fructosyl-lysine and advanced glycation end products in the kidney, retina and peripheral nerve of streptozotocin-induced diabetic rats. Biochem Soc Trans. 2003 Dec;31(Pt 6):1423-5.
| Cas No. | 21291-40-7 | SDF | |
| 别名 | 果糖-赖氨酸; Fructoselysine | ||
| Canonical SMILES | N[C@H](C(O)=O)CCCCNCC([C@@H](O)[C@H](O)[C@H](O)CO)=O | ||
| 分子式 | C12H24N2O7 | 分子量 | 308.33 |
| 溶解度 | 储存条件 | ||
| 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 | 3.2433 mL | 16.2164 mL | 32.4328 mL |
| 5 mM | 0.6487 mL | 3.2433 mL | 6.4866 mL |
| 10 mM | 0.3243 mL | 1.6216 mL | 3.2433 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 |
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| % 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。
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Accumulation of Fructosyl-lysine and advanced glycation end products in the kidney, retina and peripheral nerve of streptozotocin-induced diabetic rats
Biochem Soc Trans 2003 Dec;31(Pt 6):1423-5.PMID:14641079DOI:10.1042/bst0311423.
The accumulation of AGEs (advanced glycation end products) in diabetes mellitus has been implicated in the biochemical dysfunction associated with the chronic development of microvascular complications of diabetes--nephropathy, retinopathy and peripheral neuropathy. We investigated the concentrations of Fructosyl-lysine and AGE residues in protein extracts of renal glomeruli, retina, peripheral nerve and plasma protein of streptozotocin-induced diabetic rats and normal healthy controls. Glycation adducts were determined by LC with tandem MS detection. In diabetic rats, the Fructosyl-lysine concentration was increased markedly in glomeruli, retina, sciatic nerve and plasma protein. The concentrations of N (epsilon)-carboxymethyl-lysine and N (epsilon)-carboxyethyl-lysine were increased in glomeruli, sciatic nerve and plasma protein, and N(epsilon)-carboxymethyl-lysine also in the retina. Hydroimidazolone AGEs derived from glyoxal, methylglyoxal and 3-deoxylglucosone were major AGEs quantitatively. They were increased in the retina, nerve, glomeruli and plasma protein. AGE accumulation in renal glomeruli, retina, peripheral nerve and plasma proteins is consistent with a role for AGEs in the development of nephropathy, retinopathy and peripheral neuropathy in diabetes. High-dose therapy with thiamine and Benfotiamine suppressed the accumulation of AGEs, and is a novel approach to preventing the development of diabetic complications.
Extending the HSA-Cys34-Adductomics Pipeline to Modifications at Lys525
Chem Res Toxicol 2021 Dec 20;34(12):2549-2557.PMID:34788011DOI:10.1021/acs.chemrestox.1c00311.
We previously developed an adductomics pipeline that employed nanoflow liquid chromatography and high-resolution tandem mass spectrometry (nLC-HR-MS/MS) plus informatics to perform an untargeted detection of modifications to Cys34 in the tryptic T3 peptide of human serum albumin (HSA) (21ALVLIAFAQYLQQC34PFEDHVK41). In order to detect these peptide modifications without targeting specific masses, the pipeline interrogates MS2 ions that are signatures of the T3 peptide. The pipeline had been pilot-tested with archived plasma from healthy human subjects, and several of the 43 Cys34 adducts were highly associated with the smoking status. In the current investigation, we adapted the pipeline to include modifications to the ε-amino group of Lys525─a major glycation site in HSA─and thereby extend the coverage to products of Schiff bases that cannot be produced at Cys34. Because trypsin is generally unable to digest proteins at modified lysines, our pipeline detects miscleaved tryptic peptides with the sequence 525KQTALVELVK534. Adducts of both Lys525 and Cys34 are measured in a single nLC-HR-MS/MS run by increasing the mass range of precursor ions in MS1 scans and including both triply and doubly charged precursor ions for collision-induced dissociation fragmentation. For proof of principle, we applied the Cys34/Lys525 pipeline to archived plasma specimens from a subset of the same volunteer subjects used in the original investigation. Twelve modified Lys525 peptides were detected, including products of glycation (Fructosyl-lysine plus advanced-glycated-end products), acetylation, and elimination of ammonia and water. Surprisingly, the carbamylated and glycated adducts were present at significantly lower levels in smoking subjects. By including a larger class of in vivo nucleophilic substitution reactions, the Cys34/Lys525 adductomics pipeline expands exposomic investigations of unknown human exposure to reactive electrophiles derived from both exogenous and endogenous sources.
Apparent ileal digestibility of Maillard reaction products in growing pigs
PLoS One 2018 Jul 5;13(7):e0199499.PMID:29975743DOI:10.1371/journal.pone.0199499.
The absorption of Maillard reaction products (MRP) from dietary origin has been linked to the occurrence of chronic diseases. The aim of the present study was to determine the effects of toasting time of rapeseed meal (RSM) and the processing method of the diets (pelleting and extrusion) that included RSM on the apparent ileal digestibility (AID) of total lysine, Fructosyl-lysine (FL), carboxymethyl-lysine (CML), carboxyethyl-lysine (CEL), lanthionine (LAN) and lysinoalanine (LAL) in growing pigs. The study consisted of a 2×3 factorial design with toasting time of RSM (60, 120 min) and diet processing method (mash, pelleted, extruded) as factors. Fifty growing pigs were individually fed one of the experimental diets for 4.5 consecutive days. Following euthanasia, samples of digesta were collected from the terminal 1.5 m of the small intestine. Increasing the toasting time of RSM increased the contents of FL, CML and CEL, whereas the additional effects of the diet processing methods were relatively small. Lysinoalanine and lanthionine were not detected in the diets; therefore, digestibility of these compounds could not be determined. The contents of FL, CML and CEL in the ileal chyme were positively correlated to their contents in the diets. The AID of the MRP from thermally-treated RSM were overall low and were not related to their contents in the diets. The AID of FL ranged between -8.5 and 19.1%, whilst AID of CML and CEL ranged from -0.2 to 18.3 and 3.6 to 30%, respectively. In conclusion, thermal treatments have clear effects on the contents of MRP in the diets. These compounds have relatively low digestibility in growing pigs.