N-(Benzyloxycarbonyl)-D-tryptophan

HCID 700663

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Basic information

CAS: 2279-15-4
Standard SMILES: O=C(N[C@H](Cc1c[nH]c2ccccc12)C(=O)O)OCc1ccccc1
InChIKey: AHYFYYVVAXRMKB-QGZVFWFLSA-N
Molecular formula: C19H18N2O4
Average molar mass: 338.4 g/mol
Monoisotopic mass: 338.12665706

Names & identifiers

Preferred name: N-(Benzyloxycarbonyl)-D-tryptophan
IUPAC: (2R)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
English name: N-Cbz-D-Tryptophan
Molecular formula: C19H18N2O4
Molecular weight: 338.36

Names & synonyms

2279-15-4N-(Benzyloxycarbonyl)-D-tryptophanRefChem:362590Z-D-Trp-OHN-Cbz-D-TryptophanCbz-D-Trp-OH(R)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoic acidMFCD00037945((Benzyloxy)carbonyl)-D-tryptophan(2R)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acidCHEMBL65134Z-D-TRYPTOPHAN

Show more names

Nα-Carbobenzoxy-D-tryptophanSBB00653297240_FLUKA408506_ALDRICHCbz-D-Tryptphan

M03039Nalpha-Cbz-D-tryptophann-[(benzyloxy)carbonyl]-d-tryptophanD-Tryptophan, N-[(phenylmethoxy)carbonyl]-Cbz-D-TrpZ-DTrp-OHCBZ-D-TRYPTOPHANZ-(D)-Trp-OH

Database identifiers

CAS: 2279-15-4
PubChem CID: 700663
DTXSID: DTXSID701297570
ChEMBL: CHEMBL65134
Nikkaji: J253.119D

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 91.4 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 7
Heavy atoms: 25
Formal charge: 0
Complexity: 464

Physicochemical properties

Melting point: 122 · 122-124°C
Boiling point: 619.1 · 619.1±55.0 °C(Predicted)
Density: 1.341 · 1.341±0.06 g/cm3(Predicted)
refractive index: 11 ° · 11 ° (C=1, MeOH)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: soluble in Methanol
form: powder to crystal
pka: 3.98 · 3.98±0.10(Predicted)
color: White to Light yellow to Light orange
BRN: 96744 · 96744
CAS DataBase Reference: 2279 · 2279-15-4(CAS DataBase Reference)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 280 · P280-P305+P351+P338
Risk Statements: 22 · 22/22-36/37/38
Safety Statements: 22 · 22-24/25-44-35-28-7-4
HazardClass: IRRITANT
HS Code: 29339900 · 29339900

Safety & regulation

Safety data

hs_code: 29339900
risk_code: 22/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25-44-35-28-7-4
hazard_class: IRRITANT
Hazard statements: H302
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications · 1 item

UsesNα-Cbz-D-tryptophan is an N-Cbz-protected form of D-Tryptophan (T947205). D-Tryptophan is an unnatural isomer of L-Tryptophan (T947210) and is classified as an essential amino acid. D-Tryptophan has been synthesized as part of some potent Oxytocin (Acetate: O878500) antagonists that treat preterm labour.