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Merck
CN

B1936

Sigma-Aldrich

Borrelidin

from Streptomyces sp., ≥95% (HPLC), lyophilized powder

别名:

2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid, Borrelidine, Cyclopentanecarboxylic acid, NSC 216128, Treponemycin

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关于此项目

经验公式（希尔记法）:
C28H43NO6
化学文摘社编号:
7184-60-3
分子量:
489.64
MDL编号:
MFCD01740784
UNSPSC代码:
12352200
PubChem化学物质编号:
24724413

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生物来源

Streptomyces sp.

方案

≥95% (HPLC)

表单

lyophilized powder

溶解性

DMF: soluble
DMSO: soluble
ethanol: soluble
ethyl acetate: soluble
methanol: soluble

抗生素抗菌谱

viruses

作用机制

enzyme | inhibits

储存温度

2-8°C

SMILES字符串

[H][C@]1(CCC[C@H]1C(O)=O)[C@@H]2C\C=C\C=C(C#N)[C@H](O)[C@@H](C)C[C@H](C)C[C@H](C)C[C@H](C)[C@@H](O)CC(=O)O2

InChI

1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1

InChI key

OJCKRNPLOZHAOU-UGKRXNSESA-N

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一般描述

Chemical structure: macrolide

生化/生理作用

Borrelidin is a potent angiogenesis inhibitor that induces apoptosis in capillary tube-forming cells. Also displays antimalarial activity against drug-resistant Plasmodia. Antimicrobial and selective threonyl t-RNA synthetase inhibitor.

储存分类代码

13 - Non Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
105K1097

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Chong-Xi Liu et al.
Journal of agricultural and food chemistry, 60(5), 1251-1257 (2012-01-17)
In this study, an endophytic Streptomyces sp. neau-D50 with strong antifungal activity against Phytophthora sojae was isolated from healthy soybean root, using an in vitro screening technique. A bioactivity-guided approach was then employed to isolate and determine the chemical identity
Katherine E Jackson et al.
International journal for parasitology, 42(2), 177-186 (2012-01-10)
The causative agent of malaria, Plasmodium, possesses three translationally active compartments: the cytosol, the mitochondrion and a relic plastid called the apicoplast. Aminoacyl-tRNA synthetases to charge tRNA are thus required for all three compartments. However, the Plasmodiumfalciparum genome encodes too
Tohru Nagamitsu et al.
Organic letters, 6(11), 1865-1867 (2004-05-21)
The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is SmI(2)-mediated intramolecular Reformatsky-type reaction for macrocyclization after esterification between two segments. The two key segments were synthesized through chelation-controlled carbotitanation, chelation-controlled hydrogenation, stereoselective Reformatsky
Barrie Wilkinson et al.
Bioorganic & medicinal chemistry letters, 16(22), 5814-5817 (2006-09-12)
A set of novel borrelidin analogues have been prepared by precursor-directed biosynthesis. Structure-activity relationship analysis suggests that steric structural arrangement within the C17 side chain is important for differentiating cytotoxic and anti-angiogenic activities. A C17-cyclobutyl analogue 3 was found to
Kira J Weissman
Trends in biotechnology, 25(4), 139-142 (2007-02-20)
Mutasynthesis couples the power of chemical synthesis with molecular biology to generate derivatives of medicinally valuable, natural products. Recently, this technique has been exploited by Cambridge-based biotech company Biotica Technology Ltd, and their collaborators, to generate promising new variants of
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