Structure-activity relationship of daptomycin analogues with substitution at (2S, 3R) 3-methyl glutamic acid position

被引：19

作者：

Lin, Du'an ^{[1
]}

Lam, Hiu Yung ^{[1
]}

Han, Wenbo ^{[1
]}

Cotroneo, Nicole ^{[2
]}

Pandya, Bhaumik A. ^{[2
]}

Li, Xuechen ^{[1
]}

机构：

[1] Univ Hong Kong, State Key Lab Synthet Chem, Dept Chem, Hong Kong, Hong Kong, Peoples R China

[2] Cubist Pharmaceut Inc, 55 Hayden Ave, Lexington, MA 02421 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 03期

关键词：

Daptomycin; Structure-activity relationship; Solid phase peptide synthesis; Antibiotics; Methyl glutamic acid; ALPHA-AMINO-ACIDS; ANTIBIOTICS; SERINE;

D O I：

10.1016/j.bmcl.2016.12.046

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Daptomycin is a highly effective lipopeptide antibiotic against Gram-positive pathogens. The presence of (2S, 3R) 3-methyl glutamic acid (mGlu) in daptomycin has been found to be important to the antibacterial activity. However the role of (2S, 3R) mGlu is yet to be revealed. Herein, we reported the syntheses of three daptomycin analogues with (2S, 3R) mGlu substituted by (25, 3R) methyl glutamine (mGln), dimethyl glutamic acid and (25, 3R) ethyl glutamic acid (eGlu), respectively, and their antibacterial activities. The detailed synthesis of dimethyl glutamic acid was also reported. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：456 / 459

页数：4

共 50 条

[1] Glutamate transporter blockers:: enantiomerically pure (2S,3S) and (2S,3R)-3-methyl glutamic acids
Wehbe, J
Rolland, V
Roumestant, ML
Martinez, J
[J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (09) : 1123 - 1126
[2] Biosynthesis of the (2S,3R)-3-methyl glutamate residue of nonribosomal lipopeptides
Milne, Claire
Powell, Amanda
Jim, John
Al Nakeeb, Majid
Smith, Colin P.
Micklefield, Jason
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) : 11250 - 11259
[3] Biosynthesis of the (2S,3R)-3-methyl glutamate residue of nonribosomal lipopeptides
Milne, Claire
Powell, Amanda
Jim, John
Al Nakeeb, Majid
Smith, Colin P.
Micklefield, Jason
[J]. Journal of the American Chemical Society, 2006, 128 (34): : 11250 - 11259
[4] Structure-Activity Relationship Study of Ionotropic Glutamate Receptor Antagonist (2S,3R)-3-(3-Carboxyphenyl)pyrrolidine-2-carboxylic Acid
Krogsgaard-Larsen, Niels
Storgaard, Morten
Moller, Charlotte
Demmer, Charles S.
Hansen, Jeanette
Han, Liwei
Monrad, Rune N.
Nielsen, Birgitte
Tapken, Daniel
Pickering, Darryl S.
Kastrup, Jette S.
Frydenvang, Karla
Bunch, Lennart
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (15) : 6131 - 6150
[5] STRUCTURE OF (2S,3R)-3-AMINO-2-PHENYLTHIOBUTANOIC ACID
NAKAI, H
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 : 1844 - 1845
[6] Stereospecific enzymatic transformation of α-ketoglutarate to (2S,3R)-3-methyl glutamate during acidic lipopeptide biosynthesis
Mahlert, Christoph
Kopp, Florian
Thirlway, Jenny
Micklefield, Jason
Marahiel, Mohamed A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) : 12011 - 12018
[7] Stereospecific enzymatic transformation of α-ketoglutarate to (2S,3R)-3-methyl glutamate during acidic lipopeptide biosynthesis
Mahlert, Christoph
Kopp, Florian
Thirlway, Jenny
Micklefield, Jason
Marahiel, Mohamed A.
[J]. Journal of the American Chemical Society, 2007, 129 (39): : 12011 - 12018
[8] Assymetric synthesis of (2S,3R)- and (2S,3S)-[2-13C;3-2H] glutamic acid
Okuma, Kosuke
Ono, Akira M.
Tsuchiya, Seiji
Oba, Makoto
Nishiyama, Kozaburo
Kainosho, Masatsune
Terauchi, Tsutomu
[J]. TETRAHEDRON LETTERS, 2009, 50 (13) : 1482 - 1484
[9] Incorporation of (2S,3S) and (2S,3R) β-methyl aspartic acid into RGD-containing peptides
Schabbert, S
Pierschbacher, MD
Mattern, RH
Goodman, M
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (10) : 3331 - 3337
[10] (+)-(1R,2S,3R)-2-[(Benzyloxycarbonyl)methyl]-3-phenylcyclopropanecarboxylic acid
Avery, Thomas D.
Greatrex, Ben W.
Taylor, Dennis K.
Tiekink, Edward R. T.
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O3344 - U4683

← 1 2 3 4 5 →