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5-Chloro-D-tryptophan

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5-Chloro-D-tryptophan
Category Others
Catalog number BBF-04664
CAS 55325-48-9
Molecular Weight 238.7
Molecular Formula C11H11ClN2O2

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

  • Specification
  • Properties
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IUPAC Name (2R)-2-amino-3-(5-chloro-1H-indol-3-yl)propanoic acid
Canonical SMILES C1=CC2=C(C=C1Cl)C(=CN2)CC(C(=O)O)N
InChI InChI=1S/C11H11ClN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m1/s1
InChI Key TUKKZLIDCNWKIN-SECBINFHSA-N
Boiling Point 476.9±45.0°C (Predicted)
Density 1.474±0.06 g/cm3 (Predicted)
1. Total synthesis and initial structure-activity relationships of longicatenamycin A
Franz von Nussbaum, Sonja Anlauf, Christoph Freiberg, Jordi Benet-Buchholz, Jens Schamberger, Thomas Henkel, Guido Schiffer, Dieter Häbich ChemMedChem. 2008 Apr;3(4):619-26. doi: 10.1002/cmdc.200700297.
Natural products have provided the majority of lead structures for marketed antibacterials. In addition, they are biological guide principles to new therapies. Nevertheless, numerous "old" classes of antibiotics such as the longicatenamycins have never been explored by chemical postevolution. Longicatenamycin A is the first defined longicatenamycin congener that has been totally synthesized and tested in pure form. This venture required the de novo syntheses of the non-proteinogenic amino acids (2S,3R)-beta-hydroxyglutamic acid (HyGlu), 5-chloro-D-tryptophan (D-ClTrp), and (S)-2-amino-6-methylheptanoic acid (hhLeu). In the key step, the sensitive HyGlu building block was coupled as a pentafluorophenyl active ester to the unprotected H-D-ClTrp-Glu-hhLeu-D-Val-D-(Cbz)Orn-OH fragment. This first total synthesis of longicatenamycin A provided new congeners of the natural product (deacetyllongicatenamycin, dechlorolongicatenamycin, and longicatenamycin-A-amide).

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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