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Merck
CN

E3389

Epiamastatin hydrochloride

≥97% (HPLC)

Synonym(s):

[(2R,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]-Val-Val-Asp hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C21H38N4O8
CAS Number:
100992-59-4
Molecular Weight:
474.55
NACRES:
NA.77
PubChem Substance ID:
24894512
UNSPSC Code:
12352202
MDL number:
MFCD00070396

Key Documents

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InChI

1S/C21H38N4O8.ClH/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27;/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33);1H/t12-,13+,15+,16+,17-;/m1./s1

SMILES string

Cl[H].CC(C)C[C@@H](N)[C@@H](O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(O)=O

InChI key

GBDUPCKQTDKNLS-TXUMRZAQSA-N

biological source

synthetic

assay

≥97% (HPLC)

form

powder

storage temp.

−20°C

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Biochem/physiol Actions

Epimer of amastatin at the 2-position. There are no reports of aminopeptidase inhibition by this epimer; on the contrary, there are suggestions that a 2S-hydroxyl group is important for the stability of an initial collision complex with the enzyme.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBZ9508
BCBD6427V
BCBR4752V
BCBK8042V
BCBB1341

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D H Rich et al.
Journal of medicinal chemistry, 27(4), 417-422 (1984-04-01)
Amastatin [(2S,3R)-3-amino-2-hydroxy-5-methylhexanoyl-L-valyl-L-valyl-L- aspartic acid] and bestatin [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-L-leucine] are slow-binding, competitive inhibitors of aminopeptidase M (AP-M) with net inhibition constants (Ki) of 1.9 X 10(-8) and 4.1 X 10(-6) M, respectively. The effect of inhibitor structure on net Ki and on

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