Synthesis of a 3-hydroxyl-free N-acetyl glucosamine disaccharide

被引:9
作者
Enugala, Ramu [1 ]
Marques, M. Manuel B. [1 ]
机构
[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, REQUIMTE CQFB, P-2829516 Caparica, Portugal
关键词
N-acetyl glucosamine; glycosylation; trichloro-ethoxycarbonyl group; glucosamine; ALLYLIC ETHERS; CARBOHYDRATE; OLIGOSACCHARIDES; DERIVATIVES; PALLADIUM; ALCOHOLS; TETRASACCHARIDE; DEPROTECTION; REGENERATION; CHEMISTRY;
D O I
10.3998/ark.5550190.0013.608
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and alternative route to a versatile N-acetyl glucosamine disaccharide building block was developed, possessing a free 3-hydroxyl group. In this strategy, the 2,2,2-trichloro-ethoxy carbonyl (Troc) group was used as an amino- and 3-hydroxyl-protecting group.
引用
收藏
页码:90 / 100
页数:11
相关论文
共 50 条
  • [31] N-acetyl D-glucosamine stimulates growth in procyclic forms of Trypanosoma brucei by inducing a metabolic shift
    Ebikeme, C. E.
    Peacock, L.
    Coustou, V.
    Riviere, L.
    Bringaud, F.
    Gibson, W. C.
    Barrett, M. P.
    PARASITOLOGY, 2008, 135 (05) : 585 - 594
  • [32] Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline-isatin hybrids
    Sharma, Manmohan
    Sharma, Sahil
    Buddhiraja, Abhishek
    Saxena, A. K.
    Nepali, Kunal
    Bedi, P. M. S.
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (10) : 4337 - 4344
  • [33] Enhancement in the lysozyme activity of the hen egg white foam matrix by cross-linking in the presence of N-acetyl glucosamine
    Marolia, KZ
    D'Souza, SF
    JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 1999, 39 (1-2): : 115 - 117
  • [34] Synthesis of a C3-symmetric (1→6)-N-acetyl-β-D-glucosamine octadecasaccharide using click chemistry
    Chen, Q
    Yang, F
    Du, YG
    CARBOHYDRATE RESEARCH, 2005, 340 (16) : 2476 - 2482
  • [35] Hypervalent iodane mediated reactions of N-acetyl enamines for the synthesis of oxazoles and imidazoles
    Xu, Kang
    Yang, Ruiqi
    Yang, Shuang
    Jiang, Cheng
    Ding, Zhenhua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (40) : 8977 - 8981
  • [36] Synthesis and Structural Analysis of Aspergillus fumigatus Galactosaminogalactans Featuring α-Galactose, α-Galactosamine and α-N-Acetyl Galactosamine Linkages
    Zhang, Yongzhen
    Gomez-Redondo, Marcos
    Jimenez-Oses, Gonzalo
    Arda, Ana
    Overkleeft, Herman S.
    van Der Marel, Gijsbert A.
    Jimenez-Barbero, Jesus
    Codee, Jeroen D. C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) : 12746 - 12750
  • [37] Modular Synthesis of Heparan Sulfate Oligosaccharides Having N-Acetyl and N-Sulfate Moieties
    Sun, Lifeng
    Chopra, Pradeep
    Boons, Geert-Jan
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (24) : 16082 - 16098
  • [38] Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions
    Yang, Yang
    Xue, Xiao-Chao
    Jin, Xiao-Feng
    Wang, Li-Jun
    Sha, Yin-Lin
    Li, Zhong-Jun
    TETRAHEDRON, 2012, 68 (35) : 7148 - 7154
  • [39] Development and evaluation of N-acetyl glucosamine-decorated vitamin-E-based micelles incorporating resveratrol for cancer therapy
    Baviskar, Premkumar S.
    Mahajan, Hitendra S.
    Chandankar, Sachin M.
    Agrawal, Yogeeta O.
    JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 2022, 78
  • [40] Modulation of articular chondrocyte proliferation and anionic glycoconjugate synthesis by glucosamine (GIcN), N-acetyl GIcN (GIcNAc) GIcN sulfate salt (GIcN.S) and covalent glucosamine sulfates (GIcN-SO4)
    Terry, D. E.
    Rees-Milton, K.
    Pruss, C.
    Hopwood, J.
    Carran, J.
    Anastassiades, T. P.
    OSTEOARTHRITIS AND CARTILAGE, 2007, 15 (08) : 946 - 956