Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant

被引：27
作者：
Bourgault, Jean Paul
Trabbic, Kevin R.
Shi, Mengchao
Andreana, Peter R. [1 ]
机构：
[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 11期
关键词：
THOMSEN-FRIEDENREICH ANTIGEN; GLYCOPEPTIDE ANTIGENS; CARBOHYDRATE ANTIGEN; BUILDING-BLOCKS; CANCER VACCINES; PROSTATE-CANCER; EFFICIENT; GLYCOSIDES; BREAST; ACIDS;
D O I：
10.1039/c4ob00128a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alpha-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a D-GalN(3) acceptor carrying a pre-installed alpha-N-hydroxysuccinimidyl moiety. The natural alpha linkage was prepared in high selectivity employing a suitably protected D-GalN(3)-thioglycoside donor with N-hydroxysuccinimide. With access to alpha-TF-ONH2, the preparation of the TF-PS A1 vaccine candidate ensued smoothly through oxime bond formation.
引用
收藏
页码：1699 / 1702
页数：4
相关论文
共 42 条
  • [21] Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens
    Keding, SJ
    Endo, A
    Danishefsky, SJ
    [J]. TETRAHEDRON, 2003, 59 (35) : 7023 - 7031
  • [22] Synthetic and immunological studies on clustered modes of mucin-related Tn and TF O-linked antigens: The preparation of a glycopeptide-based vaccine for clinical trials against prostate cancer
    Kuduk, SD
    Schwarz, JB
    Chen, XT
    Glunz, PW
    Sames, D
    Ragupathi, G
    Livingston, PO
    Danishefsky, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) : 12474 - 12485
  • [23] The use of diazabicyclo[2.2.2]octane as a novel highly selective dechloroacetylation reagent
    Lefeber, DJ
    Kamerling, JP
    Vliegenthart, JFG
    [J]. ORGANIC LETTERS, 2000, 2 (05) : 701 - 703
  • [24] 5-N,4-O-Carbonyl-7,8,9-tri-O-chloroacetyl-Protected Sialyl Donor for the Stereoselective Synthesis of α-(2→9)-Tetrasialic Acid
    Lin, Chang-Ching
    Lin, Nai-Pin
    Sahabuddin, L. Sk
    Reddy, Vijaya Raghava
    Huang, Li-De
    Hwang, Kuo Chu
    Lin, Chun-Cheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) : 4921 - 4928
  • [25] Synthesis of oxime-linked mucin mimics containing the tumor-related TN and sialyl TN antigens
    Marcaurelle, LA
    Shin, YS
    Goon, S
    Bertozzi, CR
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3691 - 3694
  • [26] DISTANCES BETWEEN 3' ENDS OF RIBOSOMAL RIBONUCLEIC-ACIDS REASSEMBLED INTO ESCHERICHIA-COLI RIBOSOMES
    ODOM, OW
    ROBBINS, DJ
    LYNCH, J
    DOTTAVIOMARTIN, D
    KRAMER, G
    HARDESTY, B
    [J]. BIOCHEMISTRY, 1980, 19 (26) : 5947 - 5954
  • [27] Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen
    Renaudet, O
    Dumy, P
    [J]. TETRAHEDRON LETTERS, 2004, 45 (01) : 65 - 68
  • [28] Expedient synthesis of aminooxylated-carbohydrates for chemoselective access of glycoconjugates
    Renaudet, O
    Dumy, P
    [J]. TETRAHEDRON LETTERS, 2001, 42 (43) : 7575 - 7578
  • [29] Lectin-epithelial interactions in the human colon
    Rhodes, Jonathan M.
    Campbell, Barry J.
    Yu, Lu-Gang
    [J]. BIOCHEMICAL SOCIETY TRANSACTIONS, 2008, 36 : 1482 - 1486
  • [30] Pilot study of a heptavalent vaccine-keyhole limpet hemocyanin conjugate plus QS21 in patients with epithelial ovarian, fallopian tube, or peritoneal cancer
    Sabbatini, Paul J.
    Ragupathi, Govind
    Hood, Chandra
    Aghajanian, Carol A.
    Juertzka, Margrit
    Lasonos, Alexia
    Hensley, Martee L.
    Spassova, Maria K.
    Ouerfelli, Ouathek
    Spriggs, David R.
    Tew, William P.
    Konner, Jason
    Clausen, Henrik
    Abu Rustum, Nadeem
    Dansihefsky, Samuel J.
    Livingston, Philip O.
    [J]. CLINICAL CANCER RESEARCH, 2007, 13 (14) : 4170 - 4177
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