Mono-BOC-cystamine
Names
Preferred IUPAC name
tert-Butyl {2-[(2-aminoethyl)disulfanyl]ethyl}carbamate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C9H20N2O2S2/c1-9(2,3)13-8(12)11-5-7-15-14-6-4-10/h4-7,10H2,1-3H3,(H,11,12)
    Key: XGHNLHVZHBSTHO-UHFFFAOYSA-N
  • InChI=1/C9H20N2O2S2/c1-9(2,3)13-8(12)11-5-7-15-14-6-4-10/h4-7,10H2,1-3H3,(H,11,12)
    Key: XGHNLHVZHBSTHO-UHFFFAOYAG
  • NCCSSCCNC(=O)OC(C)(C)C
Properties
C9H20N2O2S2
Molar mass 252.39 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mono-BOC-cystamine (mono BOC protected cystamine) is a tert-butyloxycarbonyl (BOC) derivative of cystamine used as crosslinker in biotechnology and molecular biology applications.[1] This compound was originally reported by Hansen et al.[2]

Uses

The disulfide chain allows the mono-BOC-cystamine to be easily cleaved, allowing removal of the tagging residue when desired.

Mono-BOC-cystamine is used as a crosslinker for the synthesis of cleavable photo-cross-linking reagent.[3]

Mono-BOC-cystamine is used as a crosslinker for the synthesis of a biodegradable cystamine spacer in PGA-cystamine-Gd-DO3A, which shows improved MRI contrast for breast carcinoma imaging in mice. [4]

Related compounds

References

  1. ^ Mono BOC Cystamine[permanent dead link], Anachem
  2. ^ Hansen, J. B.; Nielsen, M. C.; Ehrbar, U.; Buchardt, O. (1982). "Partially Protected Polyamines". Synthesis. 1982 (5): 404–405. doi:10.1055/s-1982-29814. Archived from the original on 2014-02-21. Retrieved 2012-04-26.
  3. ^ Peter E Nielsen, John B Hansen and Ole Buchard (1984). "Photochemical cross-linking of protein and DNA in chromatin". Biochem J: 519–526.
  4. ^ Tianyi Kea; Yi Fengb; Junyu Guoc; Dennis L. Parkerc; Zheng-Rong Lua (2006). "Biodegradable cystamine spacer facilitates the clearance of Gd(III) chelates in poly(glutamic acid) Gd-DO3A conjugates for contrast-enhanced MR imaging". Magnetic Resonance Imaging. 24 (7): 931–940. doi:10.1016/j.mri.2006.03.009. PMID 16916710.
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