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15402 Sigma-Aldrich

Boc-Dap-OH

≥98.0% (TLC)

Synonym: (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

  • CAS Number 73259-81-1

  • Empirical Formula (Hill Notation) C8H16N2O4

  • Molecular Weight 204.22

  •  Beilstein/REAXYS Number 4182136

  •  MDL number MFCD00236843

  •  eCl@ss 32160406

  •  PubChem Substance ID 57647411

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Properties

Related Categories Chemical Biology, Chemical Synthesis, DAP (2,3-Diaminopropionic Acid), Peptide Synthesis and Peptide Chemistry, Unnatural Amino Acids & Derivatives More...
Quality Level   100
assay   ≥98.0% (TLC)
optical activity   [α]20/D +5.5±1°, c = 1% in methanol: water (1:1)
application(s)   peptide synthesis: suitable
impurities   ~3% water
mp   210 °C (dec.)
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

Description

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

Packaging

1, 5 g in glass bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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