L-Isoleucinamide

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Category Others
Catalog number BBF-04746
CAS 14445-54-6
Molecular Weight 130.19
Molecular Formula C6H14N2O

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Specification

IUPAC Name (2S,3S)-2-amino-3-methylpentanamide
Canonical SMILES CCC(C)C(C(=O)N)N
InChI InChI=1S/C6H14N2O/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H2,8,9)/t4-,5-/m0/s1
InChI Key JDAMFKGXSUOWBV-WHFBIAKZSA-N

Properties

Boiling Point 250.9°C at 760 mmHg
Density 0.98 g/cm3

Reference Reading

1. Acidiphilamides A-E, Modified Peptides as Autophagy Inhibitors from an Acidophilic Actinobacterium, Streptacidiphilus rugosus
Sunghoon Hwang, Yejin Yun, Won Hoon Choi, Seung Bum Kim, Jongheon Shin, Min Jae Lee, Dong-Chan Oh J Nat Prod. 2019 Feb 22;82(2):341-348. doi: 10.1021/acs.jnatprod.8b00828. Epub 2019 Feb 8.
Five new tripeptides, acidiphilamides A-E (1-5), were discovered along with two previously reported compounds, l-isoleucinamide (6) and l-valinamide (7), from Streptacidiphilus rugosus AM-16, an acidophilic actinobacterial strain isolated from acidic forest soil. The structures of 1-5 were elucidated as modified tripeptides bearing phenylalaninol or methioninol fragments with C3-C5 acyl chains based mainly on NMR and mass spectroscopic data. The absolute configurations of the amine units were established by advanced Marfey's method and GITC (2,3,4,6-tetra- O-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization followed by LC/MS analysis. Acidiphilamides A and B (1 and 2), the first secondary metabolites isolated from the rare actinobacterial genus Streptacidiphilus, significantly inhibited autophagic flux but not proteasome activity in HeLa cells. These compounds appeared to block mainly the autophagosome-lysosome fusion step in the late stage of cellular autophagy.

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