Isolation of D(−)-2,3-diaminopropionic acid from digestive fluid of silkworm larvae, Bombyx, mori

Wada, Shyozo; Toyota, Takeshi

doi:10.1016/0006-291x(65)90150-6

Cited by 11 publications

(5 citation statements)

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“…Diaminopropionate (DAP) 3 is a nonstandard amino acid found in both prokaryotes and higher organisms (1)(2)(3). In prokaryotes, DAP is an important intermediate in the synthesis of nonribosomal peptides exhibiting antibiotic properties such as viomycin (3), capreomycin (4), and zwittermicin (5).…”

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confidence: 99%

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Crystal Structure of Escherichia coli Diaminopropionate Ammonia-lyase Reveals Mechanism of Enzyme Activation and Catalysis

Bisht

Radha

Bharath

et al. 2012

Journal of Biological Chemistry

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Background: DAPAL is a novel PLP-dependent enzyme involved in the degradation of DAP, a nonstandard amino acid. Results: Striking structural differences were observed between apo-and holo-EcDAPAL, and structure with a PLP-aminoacrylate intermediate bound at the active site was obtained. Conclusion: Enzyme undergoes apo to holo structural transitions and follows a two-base mechanism of catalysis. Significance: The results provide insights into the catalytic mechanism of DAPAL.

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confidence: 99%

“…L-DAP is the immediate precursor in the synthesis of the neurotoxin (8). High levels of D-DAP have been found in the gut of Bombyx larvae (2), which reduce drastically in the pupal stage (9).…”

mentioning

confidence: 99%

Crystal Structure of Escherichia coli Diaminopropionate Ammonia-lyase Reveals Mechanism of Enzyme Activation and Catalysis

Bisht

Radha

Bharath

et al. 2012

Journal of Biological Chemistry

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“…Curiously, the enantiomer, R-A 2 pr, is detected in the digestive fluid of silkworm larvae, Bombyx mori. 20 So both enantiomers occur in biology and the S isomer at least has important roles to play. For the chemical syntheses of the natural products and analogues, partially protected derivatives of A 2 pr are important building blocks.…”

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confidence: 99%

Novel metal complex synthons for chiral 4-azaleucine, 2,3-diaminopropanoic acid and its elaboration

Barfod¹,

Bendahl²,

Hammershøi³

et al. 1999

J. Chem. Soc., Dalton Trans.

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Efficient syntheses of chiral Co() complexes with 2,3-diaminopropanoic acid (A 2 pr) have been developed. In these complexes, the amino acid zwitterion [A 2 pr(H ϩ )O Ϫ ] is bound didentate through the carboxylate and N 2 -amine groups while the N 3 -ammonio group [pK a = 7.19(2)] is unprotected. Syntheses of Λ(ϩ) 578 -and ∆(Ϫ) 578 -[(en) 2 Co-(S-A 2 pr(H ϩ )O)]Cl 3 ؒH 2 O were effected stereoretentively from the similarly didentate aspartato complexes Λand ∆-[(en) 2 Co(S-Asp(OH)O)]Cl 2 in reaction sequences transforming the unbound β-carboxyl group into an amine by Curtius rearrangement. The absolute configuration of the Λ(ϩ) 578 -[(en) 2 Co(S-Asp(OH)O)](ClO 4 ) 2 complex was determined by X-ray crystallographic analysis and defined the absolute stereochemistry of diastereoisomers and derived products. Methylation of the N 3 -amine group of Λ(ϩ) 578 -[(en) 2 Co(S-A 2 pr(H ϩ )O)]Cl 3 ؒH 2 O gave the (S)-4azaleucine complex Λ(ϩ) 578 -[(en) 2 Co(S-A 2 pr(Me 2 H ϩ )O)](C 4 F 9 SO 3 ) 3 from which enantiopure (ϩ)-(S)-2-amino-3-(dimethylamino)propanoic acid dihydrochloride hemihydrate [=(ϩ)-(S)-A 2 pr(Me 2 )ؒ2HClؒ0.5H 2 O] was obtained upon reductive removal of the protecting Co(III) centre. Racemic 4-azaleucine was easily produced by an alternative, but also metal-dependent method and the intermediate rac-(p)-[(tren)Co(A 2 pr(Me 2 H ϩ )O)]Zn 2 Cl 7 ؒ3H 2 O obtained in a simple solid-phase synthesis by selective reduction of achiral (p)-[(tren)Co(2-amino-3-(dimethylamino)acrylyl chloride)] 3ϩ ion adsorbed on AG 50W-X2 cation exchange resin. The epimerization rate of the Λ-[(en) 2 Co(S-A 2 prO)] 2ϩ complex ion was first-order in [HO Ϫ ] [k E = 3.8 × 10 Ϫ2 dm 3 mol Ϫ1 s Ϫ1 , I = 1.00 M (NaClO 4 ), 25 ЊC] with the diastereoisomer ratio K C (=[Λ-R]/[Λ-S]) = 0.77(2) at equilibrium in 10 mM NaOH. However, no epimerization was observed after at least 3 hours in 6 M HCl at 45 ЊC.

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“…The recent discovery by Wada and Toyota (1965) of D-2,3-diaminopropionic acid in Bombyx indicates that an additional D-amino acid occurs in this species. This compound was found in high concentration (3.6 him) in the gastrointestinal fluid of fasting larvae and reported to be low when larvae were feeding.…”

Section: Resultsmentioning

confidence: 97%

The Occurrence of Certain D-Amino Acids in Insects^*

Corrigan¹,

Srinivasan²

1966

Biochemistry

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Isolation of D(−)-2,3-diaminopropionic acid from digestive fluid of silkworm larvae, Bombyx, mori

Cited by 11 publications

References 5 publications

Crystal Structure of Escherichia coli Diaminopropionate Ammonia-lyase Reveals Mechanism of Enzyme Activation and Catalysis

Crystal Structure of Escherichia coli Diaminopropionate Ammonia-lyase Reveals Mechanism of Enzyme Activation and Catalysis

Novel metal complex synthons for chiral 4-azaleucine, 2,3-diaminopropanoic acid and its elaboration

The Occurrence of Certain D-Amino Acids in Insects^*

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Isolation of D(−)-2,3-diaminopropionic acid from digestive fluid of silkworm larvae, Bombyx, mori

Cited by 11 publications

References 5 publications

Crystal Structure of Escherichia coli Diaminopropionate Ammonia-lyase Reveals Mechanism of Enzyme Activation and Catalysis

Crystal Structure of Escherichia coli Diaminopropionate Ammonia-lyase Reveals Mechanism of Enzyme Activation and Catalysis

Novel metal complex synthons for chiral 4-azaleucine, 2,3-diaminopropanoic acid and its elaboration

The Occurrence of Certain D-Amino Acids in Insects*

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The Occurrence of Certain D-Amino Acids in Insects^*