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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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Carlos Olano et al.
Chemistry & biology, 11(1), 87-97 (2004-04-29)
The biosynthetic gene cluster for the angiogenesis inhibitor borrelidin has been cloned from Streptomyces parvulus Tü4055. Sequence analysis indicates that the macrolide ring of borrelidin is formed by a modular polyketide synthase (PKS) (borA1-A6), a result that was confirmed by
Darya Habibi et al.
Investigational new drugs, 30(4), 1361-1370 (2011-06-17)
Due to the poor prognosis and limited therapeutic options for adult patients with acute lymphoblastic leukemia (ALL), development of novel therapies is much needed to prolong patient survival and increase the efficacy of their treatment. Malignant T cells need high
Borrelidin, a potent antimalarial: stage-specific inhibition profile of synchronized cultures of Plasmodium falciparum.
Aki Ishiyama et al.
The Journal of antibiotics, 64(5), 381-384 (2011-02-24)
Christian Herber et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(25), 6684-6691 (2006-06-15)
A new iterative strategy for the flexible preparation of any oligodeoxypropionate stereoisomer is presented which relies on an o-DPPB-directed copper mediated allylic substitution employing enantiomerically pure Grignard reagents; the reaction is working with perfect control over all aspects of the
Ya-Mei Gao et al.
Journal of agricultural and food chemistry, 60(39), 9874-9881 (2012-09-13)
Borrelidin has high and specific antifungal activity against Phytophthora sojae . To explore the antifungal mechanism of borrelidin against P. sojae , the relationship between the antifungal activity of borrelidin and the concentration of threonine was evaluated. The results demonstrated
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