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

页码：1877 / 1880

页数：4

共 50 条

[31] Synthesis and biological properties of C-terminal vinyl ketone pseudotripeptides
Franceschini, Christian
Trapella, Claudio
Sforza, Fabio
Gavioli, Riccardo
Marastoni, Mauro
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2013, 28 (03) : 560 - 564
[32] Practical synthesis of disulfated hirudin C-terminal related peptides
Okayama, T
Hongo, T
Nukui, E
Muramatsu, R
Hayashi, H
Morikawa, T
PEPTIDE CHEMISTRY 1995, 1996, : 129 - 132
[33] Chemical synthesis of the C-terminal region of the opioid receptorlike 1
Sato, Takeshi
Saito, Yasuhiro
Nishimura, Noriko
Aimoto, Saburo
Peptides 2004, Proceedings: BRIDGES BETWEEN DISCIPLINES, 2005, : 267 - 268
[34] SYNTHESIS AND ANALGESIC ACTIVITY OF C-TERMINAL FRAGMENT PEPTIDES OF CHOLECYSTOKININ
IUCHI, K
NITTA, M
TANAKA, T
ITO, K
MORIMOTO, Y
TSUKAMOTO, G
CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (10) : 4307 - 4313
[35] Role of C-Terminal Region of Yeast ADP/ATP Carrier 2 Protein: Dynamics of Flexible C-Terminal Arm
Ohkura, Kazuto
Hori, Hitoshi
Shinohara, Yasuo
ANTICANCER RESEARCH, 2009, 29 (11) : 4897 - 4900
[36] SYNTHESIS OF C-TERMINAL TETRAPEPTIDE SEQUENCE DERIVED FROM GLUCAGON
BEYERMAN, HC
BONTEKOE, JS
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1962, 81 (08): : 699 - &
[37] Synthesis and biological evaluation of C-terminal hydroxamide analogues of bombesin
Devin, C
Bernad, N
Cristau, M
Artis-Noel, AM
Heitz, A
Fehrentz, JA
Martinez, J
JOURNAL OF PEPTIDE SCIENCE, 1999, 5 (04) : 176 - 184
[38] SYNTHESIS OF A TRIPEPTIDE WITH A C-TERMINAL NITRILE MOIETY AND THE INHIBITION OF PROTEINASES
STUBER, W
KOSINA, H
HEIMBURGER, N
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1988, 31 (01): : 63 - 70
[39] Convenient synthesis of phosphonodipeptides containing C-terminal -aminoalkylphosphonic acids
Sun, Biyun
Xu, Jiaxi
JOURNAL OF PEPTIDE SCIENCE, 2015, 21 (07) : 615 - 619
[40] Solid phase synthesis of C-terminal carbohydrate modified enkephalins
Drouillat, B
Kellam, B
Dekany, G
Starr, MS
Toth, I
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (17) : 2247 - 2250

← 1 2 3 4 5 →