Journal of Organic Chemistry p. 7250 - 7270 (2018)
Update date:2022-09-26
Topics:
Giltrap, Andrew M.
Haeckl, F. P. Jake
Kurita, Kenji L.
Linington, Roger G.
Payne, Richard J.
Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before embarking on the synthesis of the natural products, we prepared four structurally simpler analogues. Access to both the analogues and the natural products first required the synthesis of a number of nonproteinogenic amino acids, including three β-OH amino acids that were accessed from the convenient chiral precursor Garner's aldehyde. Following the preparation of the suitably protected nonproteinogenic amino acids, the skyllamycin analogues were assembled using a solid-phase synthetic route followed by a final stage solution-phase cyclization reaction. To access the natural products (skyllamycins A-C) the synthetic route used for the analogues was modified. Specifically, linear peptide precursors containing a C-terminal amide were synthesized via solid-phase peptide synthesis. After cleavage from the resin the N-terminal serine residue was oxidatively cleaved to a glyoxyamide moiety. The target natural products, skyllamycins A-C, were successfully prepared via a final step cyclization with concomitant formation of the unusual α-OH-glycine residue. Purification and spectroscopic comparison to the authentic isolated material confirmed the identity of the synthetic natural products.
View MoreHAINAN JINYING IMPORT AND EXPORT CO. LTD
Contact:+86-898-32875423
Address:A SECTION 19TH FL, TIMES SQUARE, NO.2 GUO MAO AVENUE HAIKOU, HAINAN, P. R. OF CHINA
Contact:+86+21-58956006 15800617331
Address:402 Room, 150# Cailun Road, Zhangjiang high tech park, Shanghai
SHUNYUANSHENG BIO-PHARMTECH CO., LTD
website:https://www.whsysbio.com
Contact:--
Address:Building 13, Liandong U Valley-Wuhan Economic Innovation Valley, No. 259, Xingsan Road, Shamao Street, Hannan District, Wuhan City, Hubei Province
website:http://www.p-oled.cn/
Contact:+86-29-81101199
Address:No. 1199, Dingkunchi 3rd Road, High Tech Zone, Xi'an, Shaanxi, China,710119
Wuxi Forest Biological Co.,Ltd
Contact:+86-510-81602300
Address:Room 317,Building D, No.159 middle Chengjiang Road,Jiangyin Wuxi city.
Doi:10.1007/BF00766249
(1990)Doi:10.1039/c2jm16598h
(2012)Doi:10.1021/jo200352j
(2011)Doi:10.1039/c0ob01207f
(2011)Doi:10.1021/ja01502a066
(1960)Doi:10.1002/chem.200390056
(2003)