M6412

Sigma-Aldrich

7-Methoxycoumarin-4-acetyl-Pro-Leu-Gly-Leu-β-(2,4-dinitrophenylamino)Ala-Arg amide

≥97% (HPLC)

Synonym(s):
7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide
Empirical Formula (Hill Notation):
C49H68N14O15
CAS Number:
Molecular Weight:
1093.15
MDL number:
PubChem Substance ID:

assay

≥97% (HPLC)

form

powder

solubility

water: 1 mg/mL, clear to slightly hazy, yellow

storage temp.

−20°C

SMILES string

COc1ccc2C(CC(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(CNc4ccc(cc4N(=O)=O)N(=O)=O)C(=O)NC(C)C(=O)NC(CCCNC(N)=N)C(N)=O)=CC(=O)Oc2c1

InChI

1S/C49H68N14O15/c1-25(2)17-34(59-48(72)37-10-8-16-61(37)41(65)19-28-20-42(66)78-39-22-30(77-6)12-13-31(28)39)45(69)55-24-40(64)57-35(18-26(3)4)46(70)60-36(23-54-32-14-11-29(62(73)74)21-38(32)63(75)76)47(71)56-27(5)44(68)58-33(43(50)67)9-7-15-53-49(51)52/h11-14,20-22,25-27,33-37,54H,7-10,15-19,23-24H2,1-6H3,(H2,50,67)(H,55,69)(H,56,71)(H,57,64)(H,58,68)(H,59,72)(H,60,70)(H4,51,52,53)

InChI key

RQASLOJQHHELIQ-UHFFFAOYSA-N

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Amino Acid Sequence

MOCAc-Pro-Leu-Gly-Leu-N3-(2,4-dinitrophenyl)-L-2,3-diaminopropionyl-Ala-Arg-NH2

Packaging

1 mg in serum bottle

Application

Internally quenched substrate for the assay of matrix metalloproteinases; yields fluorescent product MOCAc-Pro-Leu-Gly.

Certificate of Analysis

Certificate of Origin

C G Knight et al.
FEBS letters, 296(3), 263-266 (1992-01-27)
(7-methoxycoumarin-4-yl)Acetyl-Pro-Leu-Gly-Leu-(3-[2,4-dinitrophenyl]-L- 2,3-diaminopropionyl)-Ala-Arg-NH2 (Mca-Pro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2) has been synthesised as a fluorogenic substrate for the matrix metalloproteinases. The highly fluorescent 7-methoxycoumarin group is efficiently quenched by energy transfer to the 2,4-dinitrophenyl group. The punctuated metalloproteinase (PUMP, EC 3.4.24.23) cleaves the substrate at the...

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