MACROCYCLIC MUSK LACTONES AND USES THEREOF, 63/182,050, No. KO4HCVVDLDFLYX7 (U.S. Pat. App. Apr. 30, 2021)

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MACROCYCLIC MUSK LACTONES AND USES THEREOF, 63/182,050, No. KO4HCVVDLDFLYX7 (U.S. Pat. App. Apr. 30, 2021)

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1/16
`
`0e
`
`Process1
`eeh1on
`Or WwAg «ss
`Cc
`
`oO
`
`OH
`
`OH
`
`OH
`
`7 ~OH
`
`oO
`
`oO
`
`oO
`
`Or
`
`O
`
`oO
`
`OH
`
`OH
`
`: ee + AANon
`
`Process 2
`
`———.|Jo _———“--
`Corresponding macrolactones
`
`FIG. 1
`
`

`2/16
`
`at
`
`**
`
`cas
`
`0 musk lactones
`
`»C16
`
`0 musk lactones
`
`.
`
`Ci?
`
`G musk lactones|
`
`
`
`eapeageipeageenettvegwegasmragagecage.
`
`2*
`
`C1s
`
`O musklactones
`
`£
`
`FIG. 2
`
`C16
`
`1 musk lactones
`
`=*
`
`ci8
`
`1 musk lactones:
`
`MS
`
`
`
`iEiiii|
`
`cis
`
`2 musk lactones
`
`oe
`
`C20
`
`”@=9odamiAwy3Est
`
`
`
`
`
`
`
`
`
`
`

`3/16
`
`a
`
`OH
`
`C18:1 (oleic acid, OA)
`
`Fatty acid hydroxylase
`
`@-1 OH-OA
`
`@-2 OH-OA
`
`@-3 OH-OA
`
`Ring closure catalyzed bylipase
`
`Methyl musk lactone
`
`Ethyl musk lactone
`
`Propyl musk lactone
`
`FIG. 3A
`
`

`4/16
`
`~~
`
`~~
`
`OH
`
`C18:2 (linoleic acid, LA)
`
`Fatty acid hydroxylase
`
`°
`
`OH
`
`OH
`
`@-2 OH-LA
`
`@-3 OH-LA
`
`Ring closure catalyzed bylipase
`
`0
`
`@-1 OH-LA
`
`9
`
`9
`
`Methyl musk lactone
`
`Ethyl musk lactone
`
`Propyl musk lactone
`
`FIG. 3B
`
`

`5/16
`
`OH
`
`C20:4 (arachidonic acid, ARA)
`
`Fatty acid hydroxylase
`
`OH
`
`9
`
`‘OH
`
`OH
`
`OH
`
`QO
`
`‘OH
`
`9
`
`OH
`
`@-1 OH-ARA
`
`«@-2 OH-ARA
`
`@-3 OH-ARA
`
`Ring closure catalyzed bylipase
`
`
`
`Methyl musk lactone
`
`Ethyl musk lactone
`
`Propyl musk lactone
`
`FIG. 3C
`
`

`6/16
`
`0
`DOO
`
`C16:0 (Palmitic acid)
`
`Fatty acid hydroxylase
`
`w@-1 OH-C16
`
`e Nk
`wr"OH
`OH
`o@-2 OH-C16
`
`«@-3 OH-C16
`
`OH
`
`Ring closure catalyzed bylipase
`
`O
`
`O
`
`Tory ory
`
`Methyl musk lactone
`
`Ethyl musk lactone
`
`Propyl musk lactone
`
`FIG. 3D
`
`

`7/16
`
`oO
`
`
`H CAAANNNOKh8 OH
`
`C17:0 (Heptadecanoic acid)
`
`Fatty acid hydroxylase
`
`oO
`9
`OH
`HaC
`9
`OH
`HsCLAAAAONYBORA HsCLAINAOh
`3
`OH
`OH
`OH
`3
`OH
`
`@-1 OH-C17
`
`@-2 OH-C17
`
`@-3 OH-C17
`
`Ring closure catalyzed by lipase
`
`H3C
`
`Oo NOD NO
`
`°
`
`O
`
`Methyl musk lactone
`
`Ethyl musk lactone
`
`Propyl musk lactone
`
`FIG. 3E
`
`

`8/16
`
`0
`AeeOOEOOEOOES‘oH
`
`C18:0 (Octadecanoic acid)
`
`Fatty acid hydroxylase
`
`OH
`0
`O
`OH
`O
`aoeOOSH OH aoeSOSH
`
`@-1 OH-C18
`
`OH
`
`@-2 OH-C18
`
`-3 OH-C18
`
`Ring closure catalyzed by lipase
`
`O
`
`O
`
`ow yy NO
`
`O
`
`Methyl musk lactone
`
`Ethyl musk lactone
`
`Propyl musklactone
`
`FIG. 3F
`
`

`é MwraaaoeAOH
`
`OH
`
`)
`
`150H palmitic acid
`
`v
`
`
`
`0
`
`0
`
`Lipase
`
`15-Methylpentadecanolide
`
`(15-Hexadecanolide)
`
`0
`
`0
`
`{4-Ethyl tetradecanolide
`0
`
`0
`
`13-Propyltridecanolide
`
`s
`
`Oo
`
`2
`
`Lipase
`¢
`DRDDAAAASL © /Hydroxylase
`OH Nw —_——_—_>
`Palmitc
`acid (C16:
`4
`OH
`40H palmiticacid
`4
`amie acid
`(616.0)
`%
`0
`OH
`4
`MAMADKADdM AAA,
`0H ——>
`
`130H palmitic acid
`
`FIG. 4
`
`

`SN +VAihou + yee10
`
`10/16
`
`5
`
`OH
`
`
`
`OH
`
`0
`
`5
`
`Lipase
`—_—_—_—_—__
`
`0
`
`0
`
`SS
`
`+
`
`0
`
`0
`
`SS
`
`FIG. 5
`
`0
`
`O
`
`+
`
`sy
`
`

`11/16
`
`LEEOo
`
` CORaTINL
`
`TERT St st
`
`Spenyeen
`
`FIG. 6
`
`

`12/16
`
`Process 1
`
`OH
`
`Process 2—
`
`OH
`
`OH
`
`5
`
`
`
`FIG. 7
`
`0
`
`oo
`
` srperrepthers
`
`nis
`
`8
`
`isi
`yerryers‘$
`ee
`lee.
`Dreprerp
`begD
`
`

`13/16
`
`— — —=
`C18:3 (y-linolenic acid, GLA)
`
`OH
`
`Fatty acid hydroxylase
`
`= = =
`w-2 OH-GLA
`
`°
`
`‘OH
`
`OH
`Ring closure catalyzed by lipase
`
`w-3 OH-GLA
`
`OH
`
`
`
`15-Propyl-(6Z,9Z, 12Z)-pentadecatrien-15-olide
`
` 0
`
`OH
`
`— ——
`w-1 OH-GLA
`
`OH
`
`OH
`
`17-Methyl-(6Z,9Z, 12Z)-heptadecatrien-17-olide
`
`16-Ethyl-(6Z,9Z, 12Z)-hexadecatrien-16-olide
`FIG. 9
`
`
`
`
`2 saathcEsay
`
` Seahtalehiniahehihpnneaincineieh
`
`cat
`
`whe
`
`
`
`

`14/16
`
`C18:3 (a-linolenic acid, ALA)
`
`OH
`
`Fatty acid hydroxylase
`
`OH
`
`W-1 OH-ALA
`
`OH
`
`Ring closure catalyzed by lipase
`
`17-Methyl-(9Z,12Z, 15Z)-heptadecatrien-17-olide
`FIG. 11
`
`
`
`
`
`
`FIG. 12
`
`

`15/16
`
`
`
`C20:3 (8Z,11Z,14Z-eicosatrienoic acid, dihomo-y-linolenic acid, DGLA)
`
`Fatty acid hydroxylase
`
`
`
`w-1 OH-DGLA
`
`OH
`
`SS
`
`ZA
`
`19-Methyl-(8Z,11Z,14Z)-
`nonadecatrien-19-olide
`
`
`
`w-2 OH-DGLA
`
`OH
`w-3 OH-DGLA
`
`
`|r closure catalyzed bylipase
`
`
`18-Ethy1-(8Z,11Z,14Z)-
`octadecatrien-18-olide
`
`17-Propyl-(82,112,142)-
`heptadecatrien-17-olide
`
`FIG. 13
`
`

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`SARS
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`
`FIG. 14
`
`

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