R

AR = Archae, B = Eubacteria; F = Fungi, A = Animalia, P = Plantae; PR = other monocellular organisms (formerly Protista) a Within this source the free b-amino acid has been found bWithin this source the b-amino acid has been found as a substructure of a natural product (e.g. alkaloid, peptide, depsipeptide); only indicated if the related natural product is not mentioned cThe source organism mentioned might not be the real producer dAlthough L-Dopa is not a proteinogenic a-amino acids, L-b-Dopa is discussed here, because of its close structural and biosynthetic relationship with L-b-Tyr and L-b-Phe e a-AiB is not a proteinogenic amino acid

68 | 1.5 b-Amino Acids in Nature Tab. 1.5.2. Natural b-amino acids related to marine and freshwater cyanobacteria.

Type

Source(s)a of related natural products nh2

CO2H

Amba 67 nh2

R js Map 68

Amha 69

co2h

co2h

Admpa 70 nh2

_co2h i-Apa 71

A: Gastropoda Dolabella auriculariaa (dolastatin D) [118].

B: Cyanobacteria Lyngbya majuscula (majusculamide C) [119]; Lyngbya majuscula/Schizothrix calcicola (dolastatin 12, 15-epi-dolastatin 12, lyngbystatin 1, 15-epi-lyngbystatin 1) [134]. A: Gastropoda Dolabella auriculariaa (dolastatins 11-12) [120].

B: Cyanobacteria Symploca laete-viridis (malevamide B) [121]; Lyngbya sp. [(2R,3R)-Amha: ulongamides A-C; (2S,3R)-Amha: ulongamides D-F] [122]. A: Gastropoda Philinopsis speciosaa [(2R,3R)-Amha: kulokekahilide-1] [123].

B: Cyanobacteria Lyngbya majuscula (dolastatin 16) [124]. A: Gastropoda Dolabella auriculariaa (dolastatin 16) [125].

B: Cyanobacteria Lyngbya confervoides (obyanamide) [126].

A: Gastropoda Dolabella auriculariaa (dolastatin 17) [127].

Aoya (Doy) 72 nh2

B: Cyanobacteria Symploca laete-viridis (malevamide C) [121]. A: Gastropoda Onchidium sp.a (onchidin) [128].

Amoa (Amoya) 73

Amoa (Amoya) 73

co2h

oh nh oh nh s co2h oh

Ahoa 75

s co2h oh

Ahoa 75

B: Cyanobacteria (microcystins) [129]; Nodularia sp. {nodularin [129], nodularin-Har [130]}. A: Porifera Theonella swinhoeia (motuporin) [131].

B: Cyanobacteria Nostoc sp. (nostophycin).

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