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. Author manuscript; available in PMC: 2010 Mar 5.
Published in final edited form as: J Nat Prod. 2007 Dec 29;71(1):22–27. doi: 10.1021/np070280x

Table 2.

Structure–Activity Relationships for All Ahp-Containing Depsipeptides with Inhibitory Activity against Trypsin or Chymotrypsina

protease inhibition (μM)
 primary structure
compound trypsin chymotrypsin residue 1 residue 2 residue 3 AHP residue 5 Thr residue 7 residue 8 side chain
micropeptin T-2016 nt 0.0025 L-Ile N-Me-L-Tyr L-Phe L-Ahp L-Phe L-Thr D-Gac-Phos
cyanopeptolin 95417 ni 0.04 L-Val NMe-Cl-L-Tyr L-Phe Ahp L-Leu L-Thr L-Gln Ac
nostopeptin BN92012 ni 0.11 L-Val NMe-L-Tyr L-Phe Ahp L-Leu L-Thr L-Gln Ac
lyngbyastatin 418 ni 0.30 L-Val NMe-Tyr Phe L-Ahp Abu L-Thr L-Htyr L-Ala D-Gac-sulfate
symplocamide A 80.2 0.38 L-Val NMe, OMe- L-Br-Tyr L-Ile Ahp L-Cit L-Thr L-Gln But
micropeptin 88A19 ni 0.40 L-Ile NMe-L-Phe L-Val Ahp HcAla L-Thr L-Glu
planktopeptin BL11251 ni 0.80 L-Ile NMe, OMe-L-Tyr L-Thr Ahp L-Leu L-Thr L-Gln L-Htyr L-Gac
cyanopeptolin 963A20 ni 0.90 L-Val NMe- L-Phe L-Leu Ahp L-Tyr L-Thr L-Asp Hex
micropeptin 10321 ni 0.96 L-Val NMe-L-Trp L-Phe Ahp L-Gln L-Thr L-Thr Gly Hex
micropeptin 88Y22 ni 1.30 L-Ile NMe-L-Phe L-Val Ahp L-Tyr L-Thr L-Glu L-Tyr Ac
nostopeptin A23 ni 1.47 L-Ile NMe-L-Tyr L-Ile Ahp L-Leu Hmp L-Gln But
nostopeptin B23 ni 1.73 L-Ile NMe-L-Tyr L-Ile Ahp L-Leu Hmp L-Gln Ac
oscillapeptin B24 nt 1.78 L-allo-Ile NMe-OMe-L-Tyr L-Ile Ahp L-7-Me-Htyr L-Thr L-Htyr D-Mgs
oscillapeptin D24 nt 1.95 L-allo-Ile NMe-L-Phe L-Ile Ahp HcAla L-Thr D-Htyr D-Mgs
oscillapeptin A25 ni 1.89 L-allo-Ile NMe-OMe-L-Tyr L-Ile Ahp L-Htyr L-Thr L-Htyr D-Mgs
planktopeptin BL10611 ni 2.10 L-Ile NMe-OMe-L-Tyr L-Thr Ahp L-Leu L-Thr L-Gln L-Leu L-Gac
micropeptin SD97926 ni 2.40 L-Val NMe-L-Tyr L-Ile Ahp L-Tyr L-Thr L-Asp Hex
oscillapeptin E24 nt 2.64 L-allo-Ile NMe-L-Phe L-Ile Ahp L-Htyr L-Thr D-Htyr D-Mgs
oscillapeptin C24 nt 2.82 L-allo-Ile NMe-L-Phe L-Ile OMe-Ahp HcAla L-Thr D-Htyr D-Mga
micropeptin T112 ni 2.85 L-Val NMe-L-Trp L-Phe Ahp L-Tyr L-Thr L-Glu Hex
micropeptin 88F19 ni 3.02 L-Ile NMe-L-Phe L-Val Ahp L-Tyr L-Thr OMe-L-Glu L-Phe But
micropeptin SD100226 ni 3.13 L-Val NMe-L-Trp L-Ile Ahp L-Tyr L-Thr L-Asp Hex
nostopeptin J27 ni 3.2 L-Ile NMe-OMe-L-Tyr L-Leu OMe-Ahp L-Leu Hmp L-Gln Ac
nostopeptin I27 ni 3.5 L-Ile NMe-OMe-L-Tyr L-Leu Ahp L-Leu Hmp L-Gln Ac
nostopeptin E27 ni 3.6 L-Ile NMe-L-Tyr L-Leu Ahp L-Leu Hmp L-Gln Ac
nostopeptin F27 ni 3.8 L-Ile NMe-L-Tyr L-Leu OMe-Ahp L-Leu Hmp L-Gln Ac
largamide F28 ni 4.00 L-Val L-NMe-Br-Tyr L-Thr L-Ahp L-Tyr L-Thr L-Val L-Ala L-Ahppa, D-Gac
micropeptin SF90929 ni 4.40 L-Ile L-NMe-Tyr L-Leu Ahp L-Gln L-Thr L-Hpla
micropeptin 88C19 ni 4.50 L-Ile NMe-L-Phe L-Val Ahp L-Tyr L-Thr L-Glu L-Phe But
micropeptin 88E19 ni 4.90 L-Ile NMe-L-Phe L-Val Ahp L-Leu L-Thr L-Glu L-Phe But
micropeptin 88D19 ni 8.96 L-Ile NMe-L-Phe L-Val Ahp HcAla L-Thr L-Glu L-Phe But
largamide D28 ni 10.00 L-Val L-NMe-Br-Tyr L-Thr L-Ahp L-Leu L-Thr L-Val L-Ala L-Ahppa, D-Gac
largamide E28 ni 10.00 L-Val L-NMe-Cl-Tyr L-Thr L-Ahp L-Leu L-Thr L-Val L-Ala L-Ahppa, D-Gac
planktopeptin BL8431 ni ni L-Ile NMe-OMe-L-Tyr L-Thr Ahp L-Leu L-Thr L-Gln L-Glu-γ-lactam
micropeptin 88N22 ni ni L-Ile NMe-L-Phe L-Val Ahp L-Tyr L-Thr L-Glu L-Leu But
largamide G28 ni ni L-Val L-NMe-Br-Tyr L-Thr L-Ahp L-Htyr L-Thr L-Val L-Ala L-Ahppa, D-Gac
nostopeptin C27 ni ni L-Ile NMe-L-Tyr L-Ile Ahp L-Leu Hmp L-Gln Ac
nostopeptin D27 ni ni L-Ile NMe-L-Tyr L-Ile Ahp L-Leu Hmp L-Gln Pr
A90720A30 0.0096 nt L-Val L-NMe-Tyr L-Leu Ahp L-Arg L-Thr D-Leu L-Gac-sulfate
micropeptin A31 0.07 ni L-Val NMe-L-Tyr L-Leu Ahp L-Arg L-Thr L-Glu Oct
micropeptin T212 0.10 ni L-Val NMe-L-Trp L-Phe Ahp L-Lys L-Thr L-Glu Hex
oscillapeptin F24 0.18 ni L-allo-Ile NMe-L-Phe L-Ile Ahp L-Lys L-Thr D-Htyr D-Mgs
micropeptin SF99529 0.20 ni L-Val L-NMe-Trp L-Ile Ahp L-Arg L-Thr L-Asp Hex
cyanopeptolin S32 0.24 nt L-Ile NMe-L-Phe L-Ile Ahp L-Arg L-Thr Gac-sulfate
micropeptin B31 0.26 ni L-Val NMe-L-Tyr L-Leu Ahp L-Arg L-Thr L-Glu Hex
micropeptin 9033 2.08 ni Val NMe-Tyr L-Phe Ahp Arg L-Thr Gac-sulfate
micropeptin EI99234 3.83 ni L-Ile NMe-L-Tyr L-Phe Ahp L-Arg L-Thr L-Asp But
micropeptin SD99926 4.00 ni L-Val NMe-L-Kyn L-Ile Ahp L-Arg L-Thr L-Asp Hex
micropeptin E196434 4.36 ni L-Ile NMe-L-Tyr L-Phe Ahp L-Arg L-Thr L-Asp Ac
micropeptin SD94426 8.47 ni L-Val NMe-L-Tyr L-Ile Ahp L-Lys L-Thr L-Asp Hex
micropeptin 88B19 ni ni L-Ile NMe-L-Phe L-Val Ahp L-Glu L-Thr L-Glu L-Phe But
a

ni = no inhibition at 10 μM or IC50 > 10 μM.

nt = not tested. Abbreviations used in this table: Ahp: 3-amino-6-hydroxy-2-piperidone; Gac-phos: glyceric acid phosphate; Gac-sulfate: glyceric acid sulfate; NMe-Cl-Tyr: N-methyl-3-chlorotyrosine; NMe-OMe-Br-Tyr: N-methyl-O-methyl-3-bromotyrosine; Ac: acetate; Abu: 2-amino-2-butenoic acid; Htyr: homotyrosine; Cit: citrulline; But: butanoic acid; HcAla: (4-hydroxy-2-cyclohexenyl)alanine; Hex: hexanoic acid; Oct: octanoic acid; N-Me-Kyn: N-methylkynurenine; Hmp: 3-hydroxy-4-methylproline; Mgs: 2-O-methylglyceric acid-3-O-sulfate; Mga: 2-O-methylglyceric acid; Ahppa: 2-amino-5-(4′-hydroxyphenyl)pentanoic acid; Hpla: p-hydroxyphenyllactic acid; Pr: propionic acid.