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Macrocycle Compounds

Macrocycle Compounds

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Growing interest towards medium- and large-sized macrocycles closely linked with the field of protein-protein interactions (PPI) as promising therapeutics targets.
ChemDiv used two methodologies for design and synthesis of macrocyclic peptidomimetic library.
One of them includes ring expansion employing Bormann-Wasserman strategy (BWS) and allows synthesising 10-12-membered lactams. This gives us access to unique functionally enriched, spiro and fused scaffolds.
The other one is based on click-macrocyclization of linear peptidomimetics bearing acetylene and azide functionalities at the ends to provide 14-22 membered macrocyclic peptidomimetics.
That allowed us to obtain novel, IP clean, diverse set of macrocyclic scaffolds that we offer for synthetic proposal.

 Please contact us at chemdiv@chemdiv.com to obtain database of novel scaffolds for evaluation and discussion of final macrocycles compounds for production.


Macrocyclic Peptidomimetics

 Our Goals:

  • The scaffolds and final compounds should be peptide mimetics;

  • The scaffolds should have at least two points of diversification, preferably in peptoid moiety;

  • The scaffolds and final compounds should be single diastereomers and, optionally, single

  • enantiomers with known configuration;

  • Selected synthetic tool for macrocyclization should be high yielding, preferably applicable for

  • liquid phase synthesis (LPS) and, optionally, for solid phase synthesis (SPS) if LPS fails to provide

  • target macrocycles in reasonable yields;

  • Reported data about structural features that are able to improve cell permeability for macrocyclic

  • peptide mimetics should be considered in the library design.


Synthetic Tool Selection:

  • Click-macro-cyclization (CMC) has obvious advantages if compared to other most used approaches such as macro-lactamization or RCM.

  • CMC is less sensitive in relation to size of cycle formed;

  • CMC is highly region-controlled with no stereo-chemical impact (in contrast to MCR that usually lead to

  • formation of cis- and trans-isomers in various ratio);

  • Triazole ring formed as a result of CMC is pharmacologically relevant: to the best of our knowledge at least no negative records for this structural moiety have been published so far;

  • There are numerous commercially/synthetically available bifunctional intermediates (azides, alkynes)

  • compatible with peptide synthesis to form linkers at CMC-step with variable linker (macrocycle formed)

  • size;

  • CMC tolerates many functional groups in pre-CMC intermediates;

  • CMC is less sensitive in relation to stereochemistry of peptoid moiety (in contrast to macro-lactamization

  • that often requires opposite configuration for amino acids to be coupled at the macrocycle formation step).


Despite obvious advantages, some issues are still actual for CMC:

  • High risk of di-, tri-meric (and even more) macrocycles formation in both, LPS and SPS.

  • High dilution technique is required at CMC-step; however, it does not guarantee only monomer cycle formation

  • Success or failure of each specific scaffold synthesis becomes known only at very late steps of the challenging multi-step synthesis    

Nevertheless, our experience on validated and pre-validated series allows us to predict the most acceptable linkers and choose preferable CMC conditions to minimize mentioned side reactions and therefore to make the chemistry feasible in liquid phase.



Macrocycle Compounds

There is growing interest towards medium- and large-sized macrocycles, which is closely linked with the field of protein-protein interactions (PPI) as promising therapeutics targets.

Our team has extensive experience in addressing your synthetic chemistry. Our custom chemistry expertise, combined with robust science and transparent business models, have allowed us to serve over 2,800 customers over the past 30 years, including pharmaceutical, cosmetics & agro companies, as well as biotechs and academia research groups.

Reasons to choose ChemDiv:

  • Reliable source for novel chemistry and ideas
  • Over 300 novel scaffolds per year
  • Flexibility, transparent communication, regular reporting, excellent infrastructure
  • Fast turn-around time
  • FSS, FTE
  • Exclusive, semi-exclusive, non-exclusive
  • Science and business-focused professionals
  • Target consideration for design
  • Integration with discovery biology and pharmacology
  • Your custom selection criteria and flexible compounds library format
  • Excellent logistics
  • Proprietary collection of building blocks
  • Development and transfer of protocols and key intermediates
  • High-throughput H-NMR, LC/MC and HPLC-based purification
  • ChemDiv ensures resupply, resynthesis, immediate analogs selection, chemistry FTE, medchem FTE support for H2L.

For more details on prices, time, or research specificity - please contact chemdiv@chemdiv.com or call us:

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