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Merck
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Documentos

15402

Sigma-Aldrich

Boc-Dap-OH

≥98.0% (TLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C8H16N2O4
Número de CAS:
73259-81-1
Peso molecular:
204.22
Beilstein/REAXYS Number:
4182136
MDL number:
MFCD00236843
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57647411
NACRES:
NA.22

assay

≥98.0% (TLC)

form

solid

optical activity

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

reaction suitability

reaction type: Boc solid-phase peptide synthesis

impurities

~3% water

mp

210 °C (dec.)

application(s)

peptide synthesis

SMILES string

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

InChI key

KRJLRVZLNABMAT-YFKPBYRVSA-N

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Application

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

Other Notes

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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;
F. Ruan et al.
The Journal of Organic Chemistry, 56, 4347-4347 (1991)
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

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