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Fmoc-Thr[GalNAc(Ac)3-α-D]-OH (Fmoc-Thr(AcAcNH-α-Gal)-OH) Sale

(Synonyms: N-芴甲氧羰基-O-BETA-(2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-ALPHA-D-吡喃半乳糖基)-L-苏氨酸,Fmoc-Thr(Ac?AcNH-α-Gal)-OH) 目录号 : GC31758

Fmoc-Thr[GalNAc(Ac)3-α-D]-OH (Fmoc-Thr(AcAcNH-α-Gal)-OH) 是开发癌症疫苗的基础。

Fmoc-Thr[GalNAc(Ac)3-α-D]-OH (Fmoc-Thr(AcAcNH-α-Gal)-OH) Chemical Structure

Cas No.:116783-35-8

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25mg
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50mg
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100mg
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Sample solution is provided at 25 µL, 10mM.

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产品描述

AZP-531 is an analogue of unacylated ghrelin designed to improve glycaemic control and reduce weight.

The O-glycosidic linkage and the O-acetyl protection in this building block is stable to both piperidine and TFA, making it completely compatible with standard protocols in Fmoc solid phase peptide synthesis. The Tn antigen is a tumor-associated carbohydrate antigen that is not normally expressed in peripheral tissues or blood cells. Expression of this antigen, which is found in a majority of human carcinomas of all types, arises from a blockage in the normal O-glycosylation pathway in which glycans are extended from the common precursor GalNAcα1-O-Ser/Thr (Tn +antigen). This precursor is generated in the Golgi apparatus on newly synthesized glycoproteins by a family of polypeptide α- N-acetylgalactosaminyltransferases (ppGalNAcTs) and then extended to the common core 1 O-glycan Galβ1-3GalNAcα1-OSer/Thr (T antigen) by a single enzyme termed the T-synthase (core 1 β3-galactosyltransferase or C1GalT). Formation of the active form of the T-synthase requires a unique molecular chaperone termed Cosmc, encoded by Cosmc on the X-chromosome[1].

[1]. Ju T, et al. The Cosmc connection to the Tn antigen in cancer. Cancer Biomark. 2014 Jan 1;14(1):63-81.

Chemical Properties

Cas No. 116783-35-8 SDF
别名 N-芴甲氧羰基-O-BETA-(2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-ALPHA-D-吡喃半乳糖基)-L-苏氨酸,Fmoc-Thr(Ac?AcNH-α-Gal)-OH
分子式 C33H38N2O13 分子量 670.66
溶解度 DMSO : ≥ 100 mg/mL (149.11 mM) 储存条件 Store at -20°C
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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。
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。

溶解性数据

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1 mg 5 mg 10 mg
1 mM 1.4911 mL 7.4553 mL 14.9107 mL
5 mM 0.2982 mL 1.4911 mL 2.9821 mL
10 mM 0.1491 mL 0.7455 mL 1.4911 mL
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Research Update

Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding alpha-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac(3)GalNAc-alpha-Ser)(3)-Gly and (Ac(3)GalNAc-alpha-Thr)(3)-Gly in 27% and 49% overall yield, respectively.

A chemically synthesized version of the insect antibacterial glycopeptide, diptericin, disrupts bacterial membrane integrity

Insects protect themselves against bacterial infection by secreting a battery of antimicrobial peptides into the hemolymph. Despite recent progress, important mechanistic questions, such as the precise bacterial targets, the nature of any cooperation that occurs between peptides, and the purpose of multiple peptide isoforms, remain largely unanswered. We report herein the chemical synthesis and preliminary mechanistic investigation of diptericin, an 82 residue glycopeptide that contains regions similar to two different types of antibacterial peptides. A revised, highly practical synthesis of the precursor N(alpha)-Fmoc-Thr(Ac(3)-alpha-D-GalNAc) allowed us to produce sufficient quantities of the glycopeptide for mechanistic assays. The synthetic, full-length polypeptide proved to be active in growth inhibition assays with an IC(50) of approximately 250 nM, a concentration similar to that found in the insect hemolymph. Biological analysis of diptericin fragments indicated that the main determinant of antibacterial activity lay in the C-terminal region that is similar to the attacin peptides, although the N-terminal segment, related to the proline-rich family of antibacterial peptides, augmented that activity by 100-fold. In all assays, activity appeared glycosylation independent. Circular dichroism of unglycosylated diptericin indicated that the peptide lacked structure both in plain buffer and in the presence of liposomes. Diptericin increased the permeability of the outer and inner membranes of Escherichia coli D22 cells, suggesting possible mechanisms of action. The ability to access glycopeptides of this type through chemical synthesis will facilitate further mechanistic studies.