Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine

Lange, Meinolf; Fischer, Peter M.

doi:10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4

Cited by 8 publications

(3 citation statements)

References 18 publications

(21 reference statements)

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“…( ent - 42 ) [α] 25 D +24.8 ( c 0.25, H 2 O); 1 H NMR (500 MHz, D 2 O) δ 1.38−1.54 (m, 4H), 1.85−2.00 (m, 4H), 4.01 (t, J = 6.1 Hz, 2H); 13 C NMR (125 MHz, D 2 O) δ 23.7, 29.2, 52.8, 172.2. The spectroscopic data were consistent with those reported 25h. The melting point of this compound has not previously been reported.…”

Section: Methodssupporting

confidence: 91%

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Enantiomerically Pure α-Amino Acid Synthesis via Hydroboration−Suzuki Cross-Coupling

et al. 2002

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The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

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Section: Methodssupporting

confidence: 91%

“…Mammals lack the DAP/lysine pathway, and thus inhibitors of this pathway could provide potential antibacterial agents with low mammalian toxicity . 2,7-Diaminosuberic acid (DAS) 42 has also attracted considerable interest and has been used as a replacement for cystine in analogues of biologically active peptides …”

Section: Resultsmentioning

confidence: 99%

Enantiomerically Pure α-Amino Acid Synthesis via Hydroboration−Suzuki Cross-Coupling

et al. 2002

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“…Until recently, synthesis and incorporation of ( S , S )-2,7-diaminosuberic acid into a peptide was challenging. Several elegant approaches have recently been reported, which include Schöllkopf bislactam ether methodology, Kolbe coupling of glutamic acid derivatives, and the use of chiral auxiliaries …”

Section: Introductionmentioning

confidence: 99%

Controlled Synthesis of (S,S)-2,7-Diaminosuberic Acid: A Method for Regioselective Construction of Dicarba Analogues of Multicystine-Containing Peptides

et al. 2006

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A method to facilitate regioselective formation of multiple dicarba isosteres of cystine is described. A sequence of ruthenium-catalyzed cross metathesis and rhodium-catalyzed hydrogenation of nonproteinaceous allylglycine derivatives has been developed to achieve high-yielding and unambiguous formation of diaminosuberic acid derivatives. Allylglycine derivatives readily undergo ruthenium-catalyzed metathesis and hydrogenation to yield diaminosuberic acid derivatives in near quantitative yield. Under the same experimental conditions, prenylglycine was found to be inert to both Grubbs' and Wilkinson's catalyzed metathesis and hydrogenation, respectively, but was readily activated for metathesis via cross metathesis with Z-butene. Subsequent cross metathesis of the metathesis-formed crotylglycine derivative, followed by hydrogenation, yielded the second diaminosuberic acid derivative in excellent yield.

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Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Esters with Biscarbamate Protection and Its Application to the Synthesis of xCT Inhibitors

Yasuno

Mizutani

Sueuchi

et al. 2019

Chemistry A European J

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Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine

Cited by 8 publications

References 18 publications

Enantiomerically Pure α-Amino Acid Synthesis via Hydroboration−Suzuki Cross-Coupling

Enantiomerically Pure α-Amino Acid Synthesis via Hydroboration−Suzuki Cross-Coupling

Controlled Synthesis of (S,S)-2,7-Diaminosuberic Acid: A Method for Regioselective Construction of Dicarba Analogues of Multicystine-Containing Peptides

Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Esters with Biscarbamate Protection and Its Application to the Synthesis of xCT Inhibitors

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