Synthesis of the C-Terminal Macrocycle of Asperipin-2a

被引：5
|
作者：
Shabani, Sadegh [1 ,2 ]
White, Jonathan M. [1 ,2 ]
Hutton, Craig A. [1 ,2 ]
机构：
[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 06期
基金：
澳大利亚研究理事会;
关键词：
ANTIMITOTIC CYCLIC-PEPTIDES; FALSE SMUT BALLS; NATURAL-PRODUCTS; USTILOXIN B; LEWIS-ACID; AZIRIDINE; TRYPTOPHAN; PHENYLALANINE; CYCLIZATION;
D O I：
10.1021/acs.orglett.9b00488
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic approach to the C-terminal macrocycle of asperipin-2a is presented. Two epimers were prepared, possessing R- and S-configurations at the beta-position of Tyr(3). Comparison of NMR data of the natural product with these isomers and X-ray crystallographic data for one macrocycle support assignment of the 2S,3S-configuration of Tyr(3). Key steps in the synthesis include a stereoselective benzylic oxidation of the tyrosine residue and Lewis-acid-catalyzed ring opening of the subsequently generated aziridine.
引用
收藏
页码：1877 / 1880
页数：4
相关论文
共 50 条
  • [41] Chemoenzymatic synthesis of C-terminal peptide thioesters for chemoselective ligations
    Merkx, Remco
    Quaedflieg, Peter
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 3 - 4
  • [42] SYNTHESIS OF C-TERMINAL SEQUENCE 25-26 OF MELITTIN
    JENTSCH, J
    ZEITSCHRIFT FUR NATURFORSCHUNG PART B-CHEMIE BIOCHEMIE BIOPHYSIK BIOLOGIE UND VERWANDTEN GEBIETE, 1969, B 24 (05): : 597 - &
  • [43] Direct synthesis of phosphinopeptides containing C-terminal α-aminoalkylphosphinic acids
    Meng, Fanhua
    Xu, Jiaxi
    AMINO ACIDS, 2010, 39 (02) : 533 - 538
  • [44] SYNTHESIS OF C-TERMINAL OCTAPEPTIDE HAVING SEQUENCE PROPOSED FOR SCOTOPHOBIN
    PARR, W
    HOLZER, G
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1974, (06): : 982 - 989
  • [45] Practical synthesis of peptide C-terminal aldehyde on a solid support
    Konno, Hiroyuki
    Sema, Yoshihiro
    Ishii, Manabu
    Hattori, Yasunao
    Nosaka, Kazuto
    Akaji, Kenichi
    TETRAHEDRON LETTERS, 2013, 54 (36) : 4848 - 4850
  • [46] SYNTHESIS OF SOME C-TERMINAL ANALOGS OF PEPTIDES - ELEDOISIN AND PHYSALAEMIN
    CUIBAN, F
    CILIANU, S
    BADEA, V
    REVUE ROUMAINE DE CHIMIE, 1974, 19 (09) : 1521 - 1533
  • [47] SYNTHESIS OF C-TERMINAL PEPTIDE SEQUENCES FROM RIBONUCLEASE-A
    SHIELDS, JE
    RENNER, H
    FEDERATION PROCEEDINGS, 1966, 25 (2P1) : 797 - &
  • [48] Solid-phase synthesis of C-terminal modified peptides
    Alsina, J
    Albericio, F
    BIOPOLYMERS, 2003, 71 (04) : 454 - 477
  • [49] Synthesis of C-terminal glycopeptides via oxime resin aminolysis
    Tremblay, Thomas
    Robert-Scott, Gabrielle
    Berube, Christopher
    Carpentier, Antoine
    Voyer, Normand
    Giguere, Denis
    CHEMICAL COMMUNICATIONS, 2019, 55 (91) : 13741 - 13744
  • [50] STUDIES IN C-TERMINAL SEQUENCING - NEW REAGENTS FOR THE SYNTHESIS OF PEPTIDYLTHIOHYDANTOINS
    SHENOY, NR
    SHIVELY, JE
    BAILEY, JM
    JOURNAL OF PROTEIN CHEMISTRY, 1993, 12 (02): : 195 - 205
12345