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endo-BCN-O-PNB

  • CAS No. 1263166-91-1

  • Cat. No. CS-0084943
  • Molecule weight315.32
  • Purity≥96%
  • MDL No.MFCD19705415

*For research and further manufacturing use only, not for direct human use.

endo-BCN-O-PNB|CS-0084943

Structure of 1263166-91-1

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General Information

  • CAS No. 1263166-91-1
  • Cat. No. CS-0084943
  • Purity ≥96%
  • MDL No. MFCD19705415
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₁₇NO₅
  • Molecular Weight 315.32
  • Synonym(s) None
  • SMILES O=C(OC1=CC=C([N+]([O-])=O)C=C1)OC[C@H]2[C@@]3([H])CCC#CCC[C@@]23[H]

Description

endo-BCN-O-PNB features a strained cyclooctyne core enabling rapid, bioorthogonal conjugation under physiological conditions. The pendant para-nitrobenzyl (PNB) group provides orthogonal cleavage capability, allowing site-specific release of payloads upon mild reduction. This dual-functionality supports efficient labeling and triggered deprotection in complex biological systems.

Application

endo-BCN-O-PNB serves as a robust, bench-stable cyclooctyne derivative for bioorthogonal labeling, enabling efficient strain-promoted azide-alkyne cycloaddition (SPAAC) under physiological conditions. The PNB (pentafluorophenyl) ester group facilitates direct conjugation with primary amines, offering orthogonal reactivity and clean purification via precipitation or dialysis. Its endo-configuration enhances ring strain and reaction kinetics, making it ideal for labeling biomolecules in complex environments.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   78.67
  • LogP   3.5498
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   4

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