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15402

Sigma-Aldrich

Boc-Dap-OH

≥98.0% (TLC)

Sinonimo/i:

(S)-2-[(tert-Butoxycarbonyl)amino]-3-aminopropionic acid, (S)-3-Amino-2-(tert-butoxycarbonyl)aminopropionic acid, (S)-3-Amino-2-(tert-butoxycarbonylamino)propanoic acid, 3-Amino-(tert-butoxycarbonyl)-L-alanine, Nα-BOC-(S)-β-aminoalanine, Nα-Boc-L-β-aminoalanine, N2-(tert-Butoxycarbonyl)-(S)-2,3-diaminopropionic acid, N2-tert-Butoxycarbonyl-L-2,3-diaminopropionic acid, Nα-Boc-L-2,3-diaminopropionic acid, Boc-Dpr-OH

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About This Item

Formula empirica (notazione di Hill):
C8H16N2O4
Numero CAS:
73259-81-1
Peso molecolare:
204.22
Beilstein:
4182136
Numero MDL:
MFCD00236843
Codice UNSPSC:
12352209
eCl@ss:
32160406
ID PubChem:
57647411
NACRES:
NA.22

Livello qualitativo

100

Saggio

≥98.0% (TLC)

Forma fisica

solid

Attività ottica

[α]20/D +5.5±1°, c = 1% in methanol: water (1:1)

Impiego in reazioni chimiche

reaction type: Boc solid-phase peptide synthesis

Impurezze

~3% water

Punto di fusione

210 °C (dec.)

applicazioni

peptide synthesis

Stringa SMILE

CC(C)(C)OC(=O)N[C@@H](CN)C(O)=O

InChI

1S/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m0/s1
KRJLRVZLNABMAT-YFKPBYRVSA-N

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Categorie correlate

Applicazioni

Reactant for:
  • Protein assembly directed by synthetic molecular recognition motifs
  • Solid phase synthesis of gramicidin S cyclic analogs with antibiotic and hemolytic activities
  • Synthesis of HCV protease inhibitor modified analogs
  • Solid phase synthesis of peptidic V1a receptor agonists
  • Directed peptide assembly at lipid-water interface

Altre note

Monoprotected derivative of DAP; used e.g. in the synthesis of glucosamine synthase inhibitors, a myosin kinase inhibitor. Preparation of peptides with metal complexing groups.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCBV0419
BCBD5907V
BCBC1953V
BCBC1953
1414465

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N Kucharczyk et al.
Biochemistry, 29(15), 3668-3676 (1990-04-17)
A mechanistic investigation of the inactivation of Escherichia coli glucosamine-6-phosphate synthase by N3-(4-methoxyfumaroyl)-L-2,3-diaminopropionate (FMDP) was undertaken. On the basis of the known participation of the N-terminal cysteine residue in this process [Chmara et al. (1986) Biochim. Biophys. Acta 870, 357;
R Andruszkiewicz et al.
Journal of medicinal chemistry, 33(10), 2755-2759 (1990-10-01)
Six peptide conjugates consisting of either norvaline, methionine, or lysine and N3-(iodoacetyl)-L-2,3-diaminopropanoic acid--a strong, irreversible inactivator of bacterial and fungal glucosamine-6-phosphate synthase--were synthesized and their antibacterial and antifungal activities were evaluated. Antimicrobial potencies of these peptides were correlated with their
J T Hunt et al.
The Biochemical journal, 257(1), 73-78 (1989-01-01)
Although the amino acid residues that are important for peptide substrates of myosin light-chain kinase have been reported, those that are important for peptide inhibitors of this enzyme have not previously been investigated. Synthetic peptides based on the sequence Lys11-Lys12-Arg13-Ala-Ala-Arg16-Ala-Thr-Ser19
F. Ruan et al.
The Journal of Organic Chemistry, 56, 4347-4347 (1991)

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