Boc-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid
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Boc-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid

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Category
BOC-Amino Acids
Catalog number
BAT-007923
CAS number
58521-49-6
Molecular Formula
C13H25NO5
Molecular Weight
275.34
Boc-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid
IUPAC Name
(3S,4S)-3-hydroxy-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoic acid
Synonyms
Boc-Sta(3S,4S)-OH; (3S,4S)-4-(Boc-amino)-3-hydroxy-6-methylheptanoic acid; Boc-statine; BOC-STA-OH; (3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid; N-(t-butyloxycarbonyl)-statine; 4(S)-t-butoxycarbonylamino-3(S)-hydroxy-6-methylheptanoic acid; (3S,4S)-6-methyl-4-t-butoxycarbonylamino-3-hydroxyheptanoic acid; (3S,4S)-4-[(t-Butoxycarbonyl)amino]-3-hydroxy-6-methylheptanoic acid
Appearance
Amorphous white powder
Purity
≥ 98% (HPLC)
Density
1.107 g/cm3
Melting Point
119-122 °C
Boiling Point
440.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H25NO5/c1-8(2)6-9(10(15)7-11(16)17)14-12(18)19-13(3,4)5/h8-10,15H,6-7H2,1-5H3,(H,14,18)(H,16,17)/t9-,10-/m0/s1
InChI Key
KJIQRHBVNGRPCO-UWVGGRQHSA-N
Canonical SMILES
CC(C)CC(C(CC(=O)O)O)NC(=O)OC(C)(C)C
1. Synthesis of analogues of the carboxyl protease inhibitor pepstatin. Effects of structure on inhibition of pepsin and renin
D H Rich, E T Sun, E Ulm J Med Chem. 1980 Jan;23(1):27-33. doi: 10.1021/jm00175a006.
Analogues of the carboxyl protease inhibitor, pepstatin, were synthesized from optically pure forms of N-(tert-butoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid (Boc-Sta), and the inhibition of pepsin and renin was determined. In addition, the new amino acid (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid [AHPPA] was synthesized and the stereochemistry of the 3 and 4 positions established. The tripeptides isovaleryl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-L-alanine isoamylamide [Iva-Val-(3S,4S)-Sta-Ala-NHiC5H11] and Iva-Val-(3S,4S)-AHPPA-Ala-NHiC5H11 were found to be potent inhibitors of pepsin with Ki = 1 x 10(-9) and 0.9 x 10(-9) M, respectively. Changing the chirality of the (3S)-hydroxy group to 3R or shortening the peptide chain diminished binding to pepsin over 100-fold. Three structural requirements necessary for potent inhibition of pepsin are proposed.
2. Inhibition of cathepsin D by substrate analogues containing statine and by analogues of pepstatin
N S Agarwal, D H Rich J Med Chem. 1986 Dec;29(12):2519-24. doi: 10.1021/jm00162a015.
Five new cathepsin D inhibitors were synthesized and tested as inhibitors of bovine cathepsin D. The compounds were derived by replacing a Phe-Phe dipeptidyl unit of a good cathepsin D substrate, Boc-Phe-Leu-Ala-Phe-Phe-Val-Leu-OR, with statine [3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid, Sta) or with Sta-Phe. The best inhibitor, Boc-Phe-Leu-Ala-(S,S)-Sta-Val-Leu-OMe, inhibited cathepsin D with a Ki value of 1.1 nM. In general, the more effective inhibitors were consistent with the proposal that statine functions as a replacement for a dipeptidyl unit. Thirty-five known pepstatin analogues also were evaluated as cathepsin D inhibitors. Substituents in the P4 and P3' positions are important for maximal inhibition of this aspartic proteinase, and the P4 substituent appears more important for inhibition of cathepsin D than for inhibition of other aspartic proteinases.
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