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B1936

Sigma-Aldrich

Borrelidin

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

Synonym(s):

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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About This Item

Empirical Formula (Hill Notation):
C28H43NO6
CAS Number:
7184-60-3
Molecular Weight:
489.64
MDL number:
MFCD01740784
UNSPSC Code:
12352200
PubChem Substance ID:
24724413

biological source

Streptomyces sp.

Assay

≥95% (HPLC)

form

lyophilized powder

solubility

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

antibiotic activity spectrum

viruses

Mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

[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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General description

Chemical structure: macrolide

Biochem/physiol Actions

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.

comparable product

Product No.
Description
Pricing

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
105K1097

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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
Carlos Olano et al.
Molecular microbiology, 52(6), 1745-1756 (2004-06-10)
The 18-membered polyketide macrolide borrelidin exhibits a number of important biological activities, including potent angiogenesis inhibition. This has prompted two recent total syntheses as well as the cloning of the biosynthetic gene cluster from Streptomyces parvulus Tü4055. Borrelidin possesses some
Steven J Moss et al.
Chemical communications (Cambridge, England), (22)(22), 2341-2343 (2006-05-31)
We report the directed biosynthesis of borrelidin analogues and their selective anti-proliferative activity against human cancer cell lines.
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
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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