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C1307

Sigma-Aldrich

Cyclo(D-Glu-Ala-D-allo-Ile-Leu-D-Trp)

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C31H44N6O7
CAS Number:
136553-74-7
Molecular Weight:
612.72
MDL number:
MFCD00144248
UNSPSC Code:
12352200
PubChem Substance ID:
24892400

assay

≥97% (HPLC)

form

solid

composition

Peptide content, >60%

storage temp.

−20°C

SMILES string

CCC(C)C1NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(Cc2c[nH]c3ccccc23)NC(=O)C(CC(C)C)NC1=O

InChI

1S/C31H44N6O7/c1-6-17(4)26-31(44)36-23(13-16(2)3)29(42)35-24(14-19-15-32-21-10-8-7-9-20(19)21)30(43)34-22(11-12-25(38)39)28(41)33-18(5)27(40)37-26/h7-10,15-18,22-24,26,32H,6,11-14H2,1-5H3,(H,33,41)(H,34,43)(H,35,42)(H,36,44)(H,37,40)(H,38,39)

InChI key

UMKHUVRCCMAOBN-UHFFFAOYSA-N

Biochem/physiol Actions

Selective ETA endothelin receptor antagonist.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
025H04581
082H05921

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K Kojiri et al.
The Journal of antibiotics, 44(12), 1342-1347 (1991-12-01)
Two endothelin (ET)-binding inhibitors, BE-18257A and BE-18257B, which antagonized 125I-ET-1 binding to a porcine aortic smooth muscle membrane, were isolated from the mycelium of a strain of Streptomyces misakiensis. These binding inhibitors were extracted with methanol from mycelium and purified
M Coles et al.
Journal of medicinal chemistry, 36(18), 2658-2665 (1993-09-03)
The selective endothelin antagonist cyclo(D-Glu-L-Ala-D-allo-Ile-L-Leu-D-Trp, BE18257B) has been synthesized via solid-phase methods and its solution conformation determined by NMR spectroscopy and simulated annealing calculations based on NOE constraints. Additional information used in the structure determination included coupling constants and chemical-shift
M Ihara et al.
Biochemical and biophysical research communications, 178(1), 132-137 (1991-07-15)
A competitive endothelin (ET) antagonist, BE-18257B, was isolated from the fermentation products of Streptomyces misakiensis. It is a novel cyclic pentapeptide, cyclo(-D-Glu-L-Ala-allo-D-Ile-L-Leu-D-Trp-), and binds to ETA receptors (ET-1 selective) in cardiovascular tissues, but not to ETB receptors (equally sensitive to
[Agonists and antagonists to endothelin receptors].
M Ihara et al.
Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme, 38(11), 1827-1840 (1993-08-01)
T Satoh et al.
FEBS letters, 310(1), 83-87 (1992-09-21)
Computer-aided molecular modelling of the endothelin (ET-A) receptor antagonists, BQ-123 and BE-18257B, shows that they have very similar 3D structures. Parts of their 3D structures are also shown to match closely with that reported for residues 6-8 in endothelin-1. On
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