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O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine | 83956-40-5

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine

英文别名

O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-serine；(2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-aminopropanoic acid

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine化学式

CAS

83956-40-5

化学式

C₁₇H₂₆N₂O₁₁

mdl

——

分子量

434.4

InChiKey

PKLDPSAWBZVIQW-YXJUNQHRSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

647.4±55.0 °C(Predicted)
密度：

1.37±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-4.5
重原子数：

30
可旋转键数：

12
环数：

1.0
sp3杂化的碳原子比例：

0.71
拓扑面积：

190
氢给体数：

3
氢受体数：

12

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester	225663-10-5	C₂₆H₄₂N₂O₁₃	590.625
——	3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester	83956-37-0	C₃₂H₃₈N₂O₁₃	658.659
——	N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester	172325-18-7	C₃₇H₄₀N₂O₁₁	688.731
——	(S)-3-((2S,3R,4R,5R,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester	945764-06-7	C₃₆H₅₀N₂O₁₁	686.8
——	O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester	225663-06-9	C₄₁H₅₄N₂O₁₀	734.887
——	benzyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate	100929-03-1	C₃₉H₄₂N₂O₁₃	746.768
——	O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester	83956-33-6	C₃₀H₃₄N₄O₁₂	642.62
——	3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate	167939-15-3	C₁₄H₁₇Cl₃N₄O₈	475.67
——	N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester	172325-03-0	C₃₅H₃₆N₄O₁₀	672.692
——	Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(pyridin-2-ylsulfanylcarbonyloxy)-tetrahydro-pyran-4-yl ester	183801-48-1	C₁₈H₂₀N₄O₉S	468.444
——	3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide	67673-39-6	C₁₂H₁₆BrN₃O₇	394.179

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(S)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid	130257-85-1	C₂₂H₃₄N₂O₁₃	534.518
——	O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine	——	C₁₁H₂₀N₂O₈	308.288
——	(S)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester	130257-88-4	C₂₆H₃₇N₃O₁₅	631.591
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-丝氨酸	N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine	120173-57-1	C₃₂H₃₆N₂O₁₃	656.643

反应信息

作为反应物：

描述：

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine 在甲醇、 sodium methylate 作用下，反应 2.0h，以94%的产率得到O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine

参考文献：

名称：

合成糖肽O-β-d-吡喃半乳糖苷-（1→3）-O-（2-乙酰氨基-2-脱氧-α-d-吡喃半乳糖醛糖基）-（1→3）-l-丝氨酸和-l-苏氨酸

摘要：

摘要在碳酸银-高氯酸银和二氯甲烷-甲苯为溶剂的条件下，存在3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-β-d-吡喃半乳糖苷氯和1-丝氨酸衍生物和-1-苏氨酸，以高的立体选择性得到N-（苄氧羰基）-3-O-（3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-α-d的苄基酯对其进行氢解和解封，得到3-O-（2-乙酰氨基-脱氧-α-d-galactopyranosyl）-l-丝氨酸和-l，将-galactopyranosyl）-l-丝氨酸（7）和-l-苏氨酸（22）。 -苏氨酸分别对应于Tn抗原的半抗原。还原7的叠氮基，随后选择性的O-去乙酰化和苄基化，得到衍生物，其被2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物糖基化以产生二糖。类似的反应顺序从22开始，给出了1-苏氨酸类似物。从两种化合物中除去保护基，得到O-β-d-吡喃半乳糖基-（1→3）-O-（2-乙酰氨基-2-脱氧

DOI：

10.1016/0008-6215(82)84033-0
作为产物：

描述：

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 在 palladium on activated charcoal calcium sulfate 、 sodium tetrahydroborate 、 silver carbonate 、 molecular sieve 、氢气、硼酸、 silver perchlorate 、 nickel dichloride 作用下，以吡啶、甲醇、乙醇、二氯甲烷、溶剂黄146 、甲苯为溶剂，反应 27.0h，生成 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine

参考文献：

名称：

合成糖肽O-β-d-吡喃半乳糖苷-（1→3）-O-（2-乙酰氨基-2-脱氧-α-d-吡喃半乳糖醛糖基）-（1→3）-l-丝氨酸和-l-苏氨酸

摘要：

摘要在碳酸银-高氯酸银和二氯甲烷-甲苯为溶剂的条件下，存在3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-β-d-吡喃半乳糖苷氯和1-丝氨酸衍生物和-1-苏氨酸，以高的立体选择性得到N-（苄氧羰基）-3-O-（3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-α-d的苄基酯对其进行氢解和解封，得到3-O-（2-乙酰氨基-脱氧-α-d-galactopyranosyl）-l-丝氨酸和-l，将-galactopyranosyl）-l-丝氨酸（7）和-l-苏氨酸（22）。 -苏氨酸分别对应于Tn抗原的半抗原。还原7的叠氮基，随后选择性的O-去乙酰化和苄基化，得到衍生物，其被2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物糖基化以产生二糖。类似的反应顺序从22开始，给出了1-苏氨酸类似物。从两种化合物中除去保护基，得到O-β-d-吡喃半乳糖基-（1→3）-O-（2-乙酰氨基-2-脱氧

DOI：

10.1016/0008-6215(82)84033-0

点击查看最新优质反应信息

文献信息

Synthesis of clustered <scp>D</scp>-GalNAc (Tn) and <scp>D</scp>-Galβ(1→3)GalNAc (T) antigenic motifs using a pentaerythritol scaffold

作者：Stephen Hanessian、Dongxu Qiu、Hubli Prabhanjan、Gurijala V. Reddy、Boliang Lou

DOI：10.1139/v96-192

日期：1996.9.1

tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Galβ(1→3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective α-glycolyl and α-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate

季戊四醇的三（氨基乙基）和三氨基衍生物已被用作支架或模板，用于通过与各自的酰胺键连接免疫相关的碳水化合物，例如 D-Galβ（1→3）GalNAc（T）和 GalNAc（Tn）。 α-乙二醇和 α-N-乙酰基-L-丝氨酸苷。这些成簇的糖苷基序旨在用作制备肿瘤特异性碳水化合物抗原和疫苗的半抗原。关键词: 糖苷合成, 2-硫代吡啶碳酸酯, 糖基供体和糖肽基序
Mirror Image Mucins and Thio Mucins with Tunable Biodegradation

作者：Victoria R. Kohout、Casia L. Wardzala、Jessica R. Kramer

DOI：10.1021/jacs.3c03659

日期：2023.8.2

heterogeneity and degradation by proteases. In this study, we describe the synthesis and study of chemically defined mucin analogues bearing native glycans. We utilized combinations of enantiomer amino acids and glycan thioether linkages to achieve tunable proteolysis while maintaining cytocompatibility and binding activity. Structural characterization revealed a previously unknown mirror-image helix

粘蛋白糖蛋白是粘液的主要成分，是细胞糖萼的组成部分。粘蛋白在健康和疾病中发挥着不同的作用，是上皮组织模型中的重要元素，并具有广泛的治疗潜力。目前，所有粘蛋白应用都面临着其固有的结构异质性和蛋白酶降解的挑战。在这项研究中，我们描述了带有天然聚糖的化学定义的粘蛋白类似物的合成和研究。我们利用对映体氨基酸和聚糖硫醚键的组合来实现可调节的蛋白水解，同时保持细胞相容性和结合活性。结构表征揭示了以前未知的镜像螺旋，并揭示了糖蛋白构象的分子驱动因素。这项工作代表了开发用于生物医学应用的人造粘蛋白的重要一步。
A Novel and Efficient Route towards α-GalNAc-Ser and α-GalNAc-Thr Building Blocks for Glycopeptide Synthesis

作者：Gottfried A. Winterfeld、Yukishige Ito、Tomoya Ogawa、Richard R. Schmidt

DOI：10.1002/(sici)1099-0690(199905)1999:5<1167::aid-ejoc1167>3.0.co;2-2

日期：1999.5
α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

作者：Maristela B. Martins-Teixeira、Vanessa L. Campo、Monica Biondo、Renata Sesti-Costa、Zumira A. Carneiro、João S. Silva、Ivone Carvalho

DOI：10.1016/j.bmc.2013.01.027

日期：2013.4

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(alpha GalNAc)Ser] 3 and cyclo[Asp-(alpha GalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids alpha GalNAc-Ser 7 or alpha GalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by a-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with alpha GalN(3)Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 mu M), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%). (C) 2013 Elsevier Ltd. All rights reserved.
Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

作者：Lajos Szabó、Jan Ramza、Courtney Langdon、Robin Polt

DOI：10.1016/0008-6215(95)00016-m

日期：1995.9

General glycosidation methodology has been developed which can selectively provide 2acetamido-2-deoxy-alpha- or beta-glycosides of beta-hydroxy-alpha-amino acid derivatives [glucopyranoside- (8, 43), galactopyranoside- (9, 13), mannopyranoside- (10), lactoside analogs (11, 38) and 3-O-beta-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic a-imino esters (Schiff bases) of L-serine and L-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl- or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete H-1- and C-13-NMR data are provided for all compounds.