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B3061

Sigma-Aldrich

Borrelidin

from Streptomyces parvulus, ≥98% (HPLC)

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:
24724417
NACRES:
NA.77

biological source

Streptomyces parvulus

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: 1 mg/mL
methanol: 1 mg/mL

antibiotic activity spectrum

viruses

Mode of action

enzyme | inhibits

shipped in

wet ice

storage temp.

−20°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.

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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András Jeney et al.
Magyar onkologia, 50(2), 93-100 (2006-08-05)
Further progress in the therapy of malignant diseases is expected from the introduction of potent antimetastatic drugs. Surveying of the complex and multi-step behavior of the metastatic process, compounds showing inhibitory action against tumor cell migration may be ranked among
Carlos Olano
The Journal of antibiotics, 64(1), 51-57 (2010-11-11)
Professor Charles Richard Hutchinson (Hutch) dedicated his research to the study of polyketide compounds, in particular, those produced by actinomycetes. Hutch principally centered his efforts to study the biosynthesis of bioactive compounds, antibiotic and antitumor drugs, and to develop new
Zhisheng Cao et al.
Bioscience, biotechnology, and biochemistry, 76(2), 353-357 (2012-02-09)
Streptomyces species strain GK18, isolated in Iran, induced deep-pitted lesions on potato tubers, lesions different from the raised lesions induced by the usual scab-causing phytotoxin, thaxtomin. In addition, neither thaxtomin production nor hybridization to its biosynthetic probe was detected for
Stereoselectivity of isolated dehydratase domains of the borrelidin polyketide synthase: implications for cis double bond formation.
Olivia Vergnolle et al.
Chembiochem : a European journal of chemical biology, 12(7), 1011-1014 (2011-04-08)
Ashoka V R Madduri et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(38), 11726-11731 (2010-08-25)
Borrelidin (1) is a polyketide that possesses extremely potent anti-angiogenesis activity. This paper describes its formal total synthesis by the most efficient route to date. This modular approach takes optimal benefit of asymmetric catalysis and permits the synthesis of analogues;
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