isomerisme
DESCRIPTION
konsep struktur dan molekulTRANSCRIPT
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KONSEP STRUKTUR MOLEKUL
& PENAMAANNYA
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Alkana
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Isomerisme
ISOMER
Senyawa dengan rumus molekul sama,
struktur berbeda. Contoh 1-butena, 2-butena.
A. Konstitusional Isomer Rumus molekul sama, berbeda gugus fungsi atau
struktur kerangka; Etanol – dimetil eter, butana-
isobutana.
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B. STEREOISOMER
Molekul yang sama tapi penyusunan atom
berbeda 3D ; α-glukosa, β-glukosa. Cis-trans.
Tdd: 1. Isomer Konformasional
2. Isomer Geometrik
3. Isomer Konfigurasional
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1. Konformasi
Disebabkan oleh perputaran relatif ikatan
tunggal. Ikatan molekul tidak rigid!
etana C2H6
Butana
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Sikloalkana
Kursi Perahu
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Contoh molekul besar :
Protein Alpha heliks
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2. Geometrik
Terjadi pada senyawa alkena dan alkana siklik
a. Cis - trans
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b. E dan Z
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3. Konfigurasi
Terjadi pada senyawa kiral
Enantiomer : pasangan senyawa kiral (bayangan
cermin)
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Contoh enantiomer
A-C dan B-D : Diastreomer
Diastereomer : steroeisomer yang bukan
pasangan bayangan cermin.
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Molekul-Meso
Jika struktur molekul tersebut adalah senyawa
yang sama (simetris planar) bukan
senyawa kiral.
Contoh diatas :meso-tartrat.
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a. Sistem D dan L
Emil fischer menggunakan gliseraldehid sebagai
standar sistem D dan L, berdasarkan orientasi
gugus OH terhadap atom C kiral.
Kanan D Kiri L
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Sistem ini umum dipakai untuk senyawa gula
dan asam amino (gugus NH2 ).
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b. Sistem R dan S
Cahn–Ingold–Prelog system
Rectus (kanan) & Sinister (kiri)
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Aturan Sistem R-S
1. Urutan penomoran gugus yang diikat oleh
atom C kiral : berdasarkan nomor atom.
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2. Ikatan rangkap diprioritaskan berdasarkan
nomor atom.
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3. Gugus dengan penomoran prioritas terendah
diposisikan di belakang (menjauhi pengamat)
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4. Jika 1 2 3 searah dengan arah jarum jam
(clockwise) : isomer R. Anticlockwise : S
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Sifat Fisik Stereoisomer
Enantiomer memiliki sifat fisik yang sama: titik
leleh, titik didih, kelarutan.
Tapi memiliki aktivitas optik dan aktivitas
farmakologis yang berbeda.
Aktivitas optik aplikasi untuk?
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Aktivitas Optik
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Alat pengukuran : polarimeter
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Polarimeter
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Pengaruh isomersime terhadap efek
obat
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Efek farmakologi enantiomer
Efek farmakologi enantiomer: Aktif, inaktif
(tidak berefek), toksik.
Hal ini disebabkan karena susunan konfigurasi
yang berbeda : sifat fisikokimia berbeda,
interaksi dengan molekul endogen/reseptor.
(hormon,enzim,DNA dll) berbeda efek
berbeda.
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Why is it important?
Untuk menghasilkan efek, molekul obat harus
berinteraksi dengan senyawa endogen/reseptor.
Interaksi dengan reseptor mirip dengan Enzim-
Substrat mekanisme lock and key.
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Contoh
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Contoh
Perisa (flavour) stereoisomer yang berlawanan
aktivitas optiknya.
Desktrorotary levorotary
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Why is it important?
Dalam dunia farmasi, banyak molekul
endogen/senyawa obat yang memiliki sifat
stereoisomerisme. Isomer-isomer tersebut
seringkali memiliki efek yang berbeda bahkan
berlawanan.
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Contoh isomerisme
Gula (sumber energi)
Adrenalin (hormon)
Penelitian mengenai stereoisomer yang
berkaitan langsung dengan efek farmakologi
yang diharapkan berkembang pesat.
Mayoritas obat berupa stereoisomer!!
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Contoh obat
Ibuprofen (analgesik, antiinflamasi)
Di pasaran: umumnya rasemat, campuran
keduanya dengan jumlah yang sama.
Efek berlawanan saling meniadakan.
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Contoh
Thalidomide : diperkenalkan thn 50-an, untuk
mengurangi morning sickness.
Teratogenik : toksik bagi fetus.
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Contoh efek toksik
• Ethambutol: Whereas one enantiomer is used
to treat tuberculosis, the other causes
blindness.
• Naproxen: One enantiomer is used to treat
arthritis pain, but the other causes liver
poisoning with no analgesic effect.
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Contoh
• Penicillin's activity is stereodependent. The
antibiotic must mimic the D-alanine chains
that occur in the cell walls of bacteria in order
to react with and subsequently inhibit
bacterial transpeptidase enzyme.
• Only L-propranolol is a powerful adrenoceptor
antagonist, whereas D-propranolol is not.
However, both have local anesthetic effect.
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Pengembangan obat
Efek farmakologi berbeda obat baru.
Fluoxetine
Rasemat : antidepresan (prozac)
Enantiomer S : anti migrain.
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Sintesis Obat Enantiomer
• Enantiopure drug is a pharmaceutical that is
available in one specific enantiomeric form.
• Without a chiral influence (for example a
chiral catalyst, solvent or starting material), a
chemical reaction that makes a chiral product
will always yield a racemate.
BAGAIMANA PEMISAHAN SENYAWA RASEMAT?
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Contoh obat di pasaran(USA)
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KONSEP KERJA OBAT
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MEKANISME KERJA OBAT
• Farmakofor & Auksofor
• Isoster dan bioisoster
• Reseptor : jenis-jenis reseptor
• Jenis ikatan dengan reseptor
• Interaksi obat reseptor
• Agonis. Antagonis.
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TUGAS
• Pemisahan rasemat : metode analisis, contoh
kasus.
• Jenis2 reseptor, interaksi obat-reseptor
gambar/ilustrasi/video.
• Bagaimana ilmuwan mengekstraksi reseptor
dari jaringan hidup? menentukan strukturnya?
Mengamati interaksinya dengan molekul
obat?
BUAT DALAM BENTUK POWER POINT
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SELAMAT BELAJAR...
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TEORI
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SELAMAT BELAJAR...