Facile synthesis of chiral N-glycosylated amino acids

被引:0
|
作者
Lin Fa Wang
Ling Qiang Kong
Li Fan
Da Cheng Yang
机构
[1] Southwest University,College of Chemistry and Chemical Engineering
来源
Research on Chemical Intermediates | 2010年 / 36卷
关键词
-Glycosylated amino acid; Fmoc-protected amino acid; Glucosamine; Chiral;
D O I
暂无
中图分类号
学科分类号
摘要
Five designed chiral glycosylated amino acids have been synthesized for the first time by coupling of 1,3,4,6-tetra-O-acetyl-β-D-glucosamine sulfate (2), previously prepared by direct acetylation of D-glucosamine hydrochloride with acetic anhydride, with chiral Fmoc-protected amino acids and DIC, HOBt, and DIEA under mild conditions. The structures of these new compounds were characterized by IR, 1H NMR, and 13C NMR spectroscopy and ESI MS.
引用
收藏
页码:237 / 243
页数:6
相关论文
共 50 条
  • [1] Facile synthesis of chiral N-glycosylated amino acids
    Wang, Lin Fa
    Kong, Ling Qiang
    Fan, Li
    Yang, Da Cheng
    RESEARCH ON CHEMICAL INTERMEDIATES, 2010, 36 (03) : 237 - 243
  • [2] A facile synthesis of N/C-terminal selenourea tethered glycosylated amino acids
    Sureshbabu, Vommina V.
    Vasantha, B.
    Madhu, C.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2013, 52 (07): : 895 - 900
  • [3] Synthesis of N-Glycosylated Soluble Fas Ligand
    Schmid, Alanca
    Bello, Claudia
    Becker, Christian F. W.
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (24)
  • [4] SYNTHESIS OF N-GLYCOSYLATED PYRIDINES AS NEW ANTIVIRAL AGENTS
    IBRAHIM, ES
    ELGEMEIE, GEH
    ABBASI, MM
    ABBAS, YA
    ELBADAWI, MA
    ATTIA, AME
    NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (06): : 1415 - 1423
  • [5] Synthesis of N-glycosylated pyridines as new antimetabolite agents
    Hussain, BA
    Attia, AM
    Elgemeie, GEH
    NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (10): : 2335 - 2343
  • [6] N-glycosylated VHH Antibodies
    Matsushita, Takahiko
    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 2023, 35 (207) : E87 - E87
  • [7] Microwave-assisted synthesis of N-glycosylated building blocks
    Paolini, Ilaria
    Nuti, Francesca
    Sabatino, Giuseppina
    Chelli, Mario
    Papini, Anna M.
    UNDERSTANDING BIOLOGY USING PEPTIDES, 2006, : 190 - +
  • [8] Reductive amination of glycosyl aldoses:: Synthesis of N-glycosylated β-glycosyl amino alcohols and their enzyme inhibitory effect
    Verma, SS
    Mishra, RC
    Tamarakar, AK
    Tripathi, BK
    Srivastava, AK
    Tripathi, RP
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2004, 23 (8-9) : 493 - 511
  • [9] Facile Synthesis of N-Methylated Amino Acids from Chiral Aziridine-2-carboxylate
    Choi, Jihye
    Ha, Hyun-Joon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01): : 7 - 8
  • [10] Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids
    Westermann, B
    Walter, A
    Flörke, U
    Altenbach, HJ
    ORGANIC LETTERS, 2001, 3 (09) : 1375 - 1378